Flavor modulator having pyridine derivative or salt thereof as active ingredient

ABSTRACT

2-(phenylalkyloxyalkyl)pyridine derivative or a 2-(phenylalkylthioalkyl)pyridine derivative imparts, when added to food and drink or cosmetics as an active ingredient, a flavor of natural impression thereto; and in particular, when added to food and drink, the compound imparts an umami imparting or enhancing, a saltiness enhancing a sweetness enhancing, and in particular, when added to a milk or dairy product, a food or drink product containing a milk or dairy product, or a dairy replacement product, the compound provides a milk richness enhancing.

This application is a Continuation of PCT International Application No.PCT/JP2016/061077, filed Apr. 5, 2016, which claims priority under 35U.S.C. Section 119(a) to Japanese Patent Application No. 2015-083656filed on Apr. 15, 2015, Japanese Patent Application No. 2015-181420filed on Sep. 15, 2015 and Japanese Patent Application No. 2015-206337filed on Oct. 20, 2015. Each of the above applications is herebyexpressly incorporated by reference, in its entirety, into the presentapplication.

BACKGROUND OF THE INVENTION Technical Field of the Invention

The present invention relates to a flavor modulator having a pyridinederivative or a salt thereof as an active ingredient. More precisely,the present invention relates to a flavor composition for foods thatuses the flavor modulator, to a food or drink product that uses theflavor modulator or the flavor composition for foods, to a flavorcomposition for cosmetics, and to a cosmetic product using the flavormodulator or the flavor composition for cosmetics. Further, the presentinvention relates to a flavor imparting or enhancing agent for food anddrink or for cosmetics that uses a pyridine derivative or a saltthereof, to an umami imparting or enhancing method for food and drink,to a sweetness enhancing method for food and drink, to a saltinessenhancing method for food and drink, to a richness enhancing method formilk, and to an emulsified composition. Further, the present inventionrelates to a powder composition using the emulsified composition.Further, the present invention relates to a novel pyridine derivative ora salt thereof.

Background Art

Recently, in flavors for food and drink and for cosmetics, there is anincreasing need for flavors having a new type of unprecedentedodor/taste with diversification of consumers' preferences, anddevelopment of unique flavor materials having mild and fresh flavorquality and excellent in sustainability is desired. Given the situation,studies for preparing flavor compositions that may feel as natural aspossible are being made by combining flavor materials adequately or withchanging the compounding ratio thereof, but could not be said to besufficient. Consequently, searches for various organic compounds as newflavor materials are being made.

Flavor compounds are compounds that stimulate a sense of smell, and itis said that tens of thousands of kinds of such compounds are known. Onthe other hand, it is considered that the flavor of food is a sense ofolfactory stimulus and taste stimulus integrated in the brain.Specifically, olfactory stimulus is combined with a compound thatstimulates a sense of taste (salt, sugar, sodium glutamate, etc.) toconstitute an entire flavor of food. Recently, among aroma compounds,those that stimulate both a sense of taste and a sense of smell aresearched for actively, and are used for improving a total flavor of foodand drink.

As a compound that stimulates both a sense of smell and a sense oftaste, for example, 4-hydroxy-2(5)-ethyl-5(2)-methyl-3(2H)-furanone hasbeen found to have an effect of enhancing saltiness when added to soysauce (Patent Document 1). In addition, 1,3,5-undecatriene has beenfound to have an additional effect of enhancing a carbonic taste similarto salt stimulation when added to carbonated drink (Patent Document 2).In general, many flavor compounds produce a bitter taste relative to asense of taste. Above all, menthol that is a typical flavor compound isknown to have a cooling taste as an olfactory stimulus effect, but apartfrom the olfactory stimulus effect, the compound is also known toproduce a cooling feel on the skin or on the mouth as a pain sensationeffect, thereby having a bitter taste as a taste stimulus effect.

Regarding umami (delicious taste) as a basic taste, compounds thatstimulate both a sense of smell and a sense of taste have been foundamong aroma compounds, and by applying these compounds as food aromas,the functionality of food and drink is expanded to provide a new tastethat consumers desire. For example, 2-alkylpyridines are disclosed tohave umami (Patent Document 3). In addition, aromatic ketone compoundshaving a pyridine ring-containing substituent (Patent Document 4) andaromatic amide compounds (PATENT DOCUMENT 5) are also disclosed as umamisubstances.

In addition, 2-(2-benzyloxyethyl)pyridine that is a kind of2-(phenylalkyloxyalkyl)pyridines is reported as a product of a nitrilecompound and acetylene in pyridine ring synthesis reaction studies(Non-Patent Document 1) and in coupling reaction studies utilizing anorganic metal (Non-Patent Document 2), and use thereof as an umamienhancer is disclosed (PATENT DOCUMENT 6).

CITATION LIST Patent Literature

PATENT DOCUMENT 1: JP 2012-70636A

PATENT DOCUMENT 2: JP 5500664B

PATENT DOCUMENT 3: JP 2011-516059T

PATENT DOCUMENT 4: JP 2012-532848T

PATENT DOCUMENT 5: JP 2014-531448T

PATENT DOCUMENT 6: WO2015/000900

Non-Patent Literature

NON-PATENT DOCUMENT 1: Izvestiya Akademii Nauk SSSR, SeriyaKhimicheskaya (1986), (7), 1628-34

NON-PATENT DOCUMENT 2: Journal of Organic Chemistry (2012), 77(22),10399-10408

SUMMARY OF INVENTION

An object of the present invention is to provide a flavor compoundwhich, when added to food and drink or to cosmetics, imparts or enhancesa favorable flavor, or when added to food and drink, imparts not only aflavor but also umami as a favorable taste and further enhances umami,sweetness, saltiness and richness of milk, and to provide a flavorcomposition containing the compound as an active ingredient, as well asa food or drink product and a cosmetic product containing the compoundas an active ingredient.

The present inventors have assiduously studied a large number of organiccompounds and, as a result, have found that a compound represented bythe following formula (1), a 2-(phenylalkyloxyalkyl)pyridine derivativeor a 2-(phenylalkylthioalkyl)pyridine derivative has a herbal, earthy,almond, nutty or rummy flavor, and regarding the taste thereof, thecompound provides, when added to food and drink in a high concentration,a somewhat bitter, vegetable-like or spicy taste, but when added theretoin a low concentration, exhibits an effect of enhancing umami,sweetness, saltiness and milk richness of food and drink, and that theeffect thereof of enhancing umami and others is significantly higherthan that of 2-(2-benzyloxyethyl)pyridine, and have completed thepresent invention.

In addition, the present inventors have further assiduously studied alarge number of organic compounds and, as a result, have found that acompound represented by the following formula (11) where the number ofcarbon atoms in the side chain on the pyridine side of the ether bond of2-(2-benzyloxyethyl)pyridine is increased by one,2-(3-benzyloxypropyl)pyridine has a herbal, green or nutty flavor ofnatural impression, and regarding the taste thereof, the compoundprovides, when added to food and drink in a high concentration, asomewhat bitter, vegetable-like or spicy taste, but when added theretoin a low concentration, exhibits an effect of enhancing umami,sweetness, saltiness and milk richness of food and drink, and that theeffect thereof of enhancing umami and others is higher by about 10 timesthan that of 2-(2-benzyloxyethyl)pyridine.

2-(3-Benzyloxypropyl)pyridine represented by the formula (11) is acompound reported in organic chemical reaction studies (Asian Journal ofOrganic Chemistry (2013), 2(12), 1061-1065; Journal of the AmericanChemical Society (2005), 127(25), 8966-8967; German Registered Patent842995), but there is no report relating to the physiological effectthereof, especially the flavor and the taste thereof, and use of thecompound as a flavor material for food and drink or for cosmetics, aswell as use thereof as an umami or sweetness enhancing agent for foodand drink is not known.

The present inventors have further assiduously studied2-(3-benzyloxypropyl)pyridine and, as a result, have found that anemulsified composition containing the compound, or a powdery compositionthereof prepared by drying the emulsified composition can be readilyincorporated in various food and drink products and in cosmetics and, inaddition, can be used as a material having a high-level flavormodulating effect.

With that, the present invention provides the following:

[1] A flavor modulator containing, as an active ingredient, a compoundrepresented by the following formula (1) or a salt thereof.

In the above formula (1), n=2, 3, 4 or 5, m=1 or 2, X represents O or S,Y represents the following formula (2) or (3).

In the above formula (2), Z represents a hydrogen atom, an alkyl grouphaving 1 to 4 carbon atoms, or a group OR (where R represents a hydrogenatom, or an alkyl group having 1 to 4 carbon atoms) (provided that acase where n=2 and m=1 is excluded). In the above formula (3), R₁ to R₅each represent a hydrogen atom or a methyl group, and at least two of R₁to R₅ are methyl groups.

[2] The flavor modulator according to [1], wherein the compoundrepresented by the formula (1) is 2-(3-benzyloxypropyl)pyridinerepresented by the following formula (11) as an active ingredient.

[3] The flavor modulator according to [1] or [2], wherein the flavormodulation is flavor impartment or enhancement.[4] The flavor modulator according to [1] or [2], wherein the flavormodulation is umami impartment.[5] The flavor modulator according to [1] or [2], wherein the flavormodulation is umami enhancement.[6] The flavor modulator according to [1] or [2], wherein the flavormodulation is sweetness enhancement.[7] The flavor modulator according to [1] or [2], wherein the flavormodulation is saltiness enhancement.[8] The flavor modulator according to [1] or [2], wherein the flavormodulation is milk richness enhancement for a milk or dairy product, afood or drink product containing a milk or dairy product, or a dairyreplacement product.[9] A flavor composition for food and drink, containing the flavormodulator according to any one of [1] to [8] as an active ingredient.[10] A food or drink product containing the flavor modulator accordingto any one of [1] to [8] or the flavor composition for food and drinkaccording to [9].[11] The flavor composition for cosmetics containing the flavormodulator according to any one of [1] to [3] as an active ingredient.[12] A cosmetic product containing the flavor modulator according to anyone of [1] to [3] or the flavor composition for cosmetics according to[11].[13] A flavor imparting or enhancing method for food and drink orcosmetics, wherein a compound represented by the formula (1) or a saltthereof in [1] is contained in a food or drink product or in a cosmeticproduct.[14] An umami imparting or enhancing method for food and drink, whereina compound represented by the formula (1) or a salt thereof in [1] iscontained in a food or drink product.[15] A sweetness enhancing method for food and drink, wherein a compoundrepresented by the formula (1) or a salt thereof in [1] is contained ina food or drink product.[16] A saltiness enhancing method for food and drink, wherein a compoundrepresented by the formula (1) or a salt thereof in [1] is contained ina food or drink product.[17] A milk richness enhancing method for a milk or dairy product, afood or drink product containing a milk or dairy product, or a dairyreplacement product, wherein a compound represented by the formula (1)or a salt thereof in [1] is contained in a milk or dairy product, a foodor drink product containing a milk or dairy product, or a dairyreplacement product.[18] An emulsified composition containing the following (A) to (D):

-   -   (A) A compound represented by the formula (1) or a salt thereof        in [1].    -   (B) Water.    -   (C) One or more selected from sugars, monoalcohols or        polyalcohols.    -   (D) An emulsifier.        [19] A powder composition produced by drying the emulsified        composition in [18].        [20] A compound represented by the following formula (4) or a        salt thereof:

In the formula (4), n=2, 3, 4 or 5, m=1 or 2, X represents 0 or S, and Yrepresents the following formula (5) or (6):

In the above formula (5), Z represents a hydrogen atom, an alkyl grouphaving 1 to 4 carbon atoms or a group OR (where R represents a hydrogenatom or an alkyl group having 1 to 4 carbon atoms) (provided that a casewhere n=2 and m=1, or a case where n=3 or 4 and m=1, X is O and Z is His excluded). In the above formula (6), R₁ to R₅ each represent ahydrogen atom or a methyl group, and at least two of R₁ to R₅ are methylgroups.

A 2-(phenylalkyloxyalkyl)pyridine derivative or a2-(phenylalkylthioalkyl)pyridine derivative, a compound represented bythe above formula (1) or a salt thereof of the compound of the presentinvention imparts, when added to food and drink or cosmetics, a herbal,green, nutty, earthy, almond or rummy flavor thereto, and in particular,when added to food and drink, imparts thereto a flavor of naturalimpression, and additionally provides an umami imparting or enhancingeffect and a sweetness and saltiness enhancing effect, and inparticular, when added to a milk or dairy product, a food or drinkproduct containing a milk or dairy product, or a dairy replacementproduct, the compound provides a milk richness enhancing effect.

2-(3-Benzyloxypropyl)pyridine, a compound of a preferred embodiment ofthe present invention provides, when added to food and drink orcosmetics, a somewhat herbal, green or natty flavor of naturalimpression, and in particular, when added to food and drink, thecompound imparts a flavor of natural impression thereto and alsoprovides an umami imparting or enhancing effect and a sweetness andsaltiness enhancing effect, and in particular, when added to a milk ordairy product, a food or drink product containing a milk or dairyproduct, or a dairy replacement product, the compound provides a milkrichness enhancing effect.

DESCRIPTION OF EMBODIMENTS

The present invention is described in more detail hereinunder.

A compound represented by the following formula (1) of the presentinvention, 2-(phenylalkyloxyalkyl)pyridine derivative or a2-(phenylalkylthioalkyl)pyridine derivative provides, as describedabove, when added to food and drink in a high concentration, a somewhatbitter, vegetable-like or spicy taste, but when added thereto in a lowconcentration, the compound provides an effect of enhancing umami,sweetness, saltiness and milk richness of food and drink.

In the above formula (1), n=2, 3, 4 or 5, m=1 or 2, X represents O or S,Y represents the following formula (2) or (3).

In the above formula (2), Z represents a hydrogen atom, an alkyl grouphaving 1 to 4 carbon atoms, or a group OR (where R represents a hydrogenatom, or an alkyl group having 1 to 4 carbon atoms) (provided that acase where n=2 and m=1 is excluded). In the above formula (3), R₁ to R₅each represent a hydrogen atom or a methyl group, and at least two of R₁to R₅ are methyl groups.

Regarding the compound represented by the above formula (1) of thepresent invention, use of a salt of the compound provides the sameeffect as the above-mentioned effect of the compound in adding to foodand drink or cosmetics. In particular, for the case of adding to foodand drink, an edible salt of the compound represented by the aboveformula (1) is preferred, for example, including hydrochlorides,phosphates, citrates, lactates, malates, gluconates, maleates,fumarates, succinates, tartrates, etc.

In particular, when Z is positioned at the para-position as shown in thefollowing formula (7), the compound provides a more favorable umami,sweetness, saltiness and milk richness enhancing effect for food anddrink.

In the above formula (7), n=2, 3, 4 or 5, m=1 or 2, X represents O or S,Y represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms,or a group OR (where R represents a hydrogen atom or an alkyl grouphaving 1 to 4 carbon atoms) (provided that a case where n=2 and m=1 isexcluded).

Specific examples of the compound include 2-(3-benzyloxypropyl)pyridine,2-(4-benzyloxybutyl)pyridine, 2-(4-benzyloxybutyl)pyridinehydrochloride, 2-(5-benzyloxypentyl)pyridine,2-(2-phenylethoxyethyl)pyridine, 2-83-phenylethoxypropyl)pyridine,2-[3-(p-methoxybenzyloxy)propyl]pyridine,2-[3-(p-ethoxybenzyloxy)propyl]pyridine,2-[3-(p-isopropyloxybenzyloxy)propyl]pyridine,2-(2-phenylethylthioethyl)pyridine, 2-(2-phenylethylthioethyl)pyridinehydrochloride, 2-(3-phenylethylthiopropyl)pyridine,2-[3-(p-methylbenzyloxy)propyl]pyridine,2-[3-(p-ethylbenzyloxy)propyl]pyridine,2-[3-(2,5-dimethylbenzyloxy)propyl]pyridine,2-[3-(2,6-dimethylbenzyloxy)propyl]pyridine. These compounds have aneffect of enhancing umami, sweetness, saltiness and milk richness offood and drink.

2-(3-Benzyloxyproyl)pyridine, a compound represented by the formula (11)is, as described above, a known compound as a substance, and can besynthesized according to the known method described in theabove-mentioned literature, but as a simpler method, the compound can bereadily produced utilizing synthesis reaction shown by the followingformula.

According to the above reaction formula, the compound can be efficientlyproduced through etherification of 2-pyridinepropanol represented by theformula (12) and benzyl chloride represented by the formula (13) in asuitable solvent in the presence of a base such as sodium hydroxide,sodium hydride, etc. The resultant compound of the formula (11) can behighly purified according to a method of distillation under reducedpressure or the like.

For example, 2-(4-benzyloxybutyl)pyridine is a known compound, and canbe prepared by utilizing synthesis reaction according to the followingscheme.

Specifically, a starting material of 2-pyridine-ethanol is chlorinatedto give 2-(2-chloroethyl)pyridine, then dimethyl2-(2-pyridyl)ethylmalonate is produced through malonate synthesis,thereafter methyl 4-(2-pyridyl)butyrate is produced through hydrolysisand decarboxylation, and this is reduced with lithium aluminium hydrideand then benzyl chloride is added thereto to give2-(4-benzyloxybutyl)pyridine.

In addition, for example, 2-(2-phenylethoxyethyl)pyridine is a novelcompound, and can be produced by utilizing synthesis reaction accordingto the following scheme.

Specifically, 2-vinylpyridine and 2-phenylethyl alcohol are reacted inthe presence of sodium hydride to prepare2-(2-phenylethoxyethyl)pyridine.

Further, for example, 2-[3-(p-methoxybenzyloxy)propyl]pyridine is anovel compound, and can be prepared utilizing synthesis reactionaccording to the following scheme.

Specifically, 2-pyridinepropanol and p-methoxybenzyl chloride arereacted in the presence of sodium hydride to prepare2-[3-(p-methoxybenzyloxy)propyl]pyridine.

These resultant compounds can be highly purified according to a methodof distillation under reduced pressure, column chromatography or thelike.

The present invention provides a flavor modulator, an umami impartingagent, an umami or sweetness enhancer, as well as a flavor compositioncontaining a compound represented by the above formula (1) or a saltthereof as an active ingredient, and a food or drink product and acosmetic product containing these.

A preferred embodiment of the present invention includes a flavormodulator, an umami imparting agent, an umami enhancer, a sweetnessenhancer, a saltiness enhancer and a milk richness enhancer, as well asa flavor composition containing 2-(3-benzyloxypropyl)pyridine as anactive ingredient, as well as a food or drink product and a cosmeticproduct containing them.

A compound represented by the above formula (1) or a salt thereof, whichis an active ingredient in the present invention, has a herbal, earthy,almond, nutty, or rummy flavor, and in the case where the compoundrepresented by the formula (1) or a salt thereof is used for flavorimpartation, it may be added to food and drink or to cosmetics in anamount generally within a range of 0.1 ppb to 200 ppm based on the massof the compound of the formula (1), preferably 1 ppb to 20 ppm, morepreferably 10 ppb to 2 ppm. By adding thereto within the concentrationrange, food and drink or cosmetics can be given a flavor of naturalimpression.

2-(3-Benzyloxypropyl)pyridine, an active ingredient in a preferredembodiment of the present invention, has a somewhat herbal or greennutty flavor of natural impression, and in the case where2-(3-benzyloxypropyl)pyridine is used for flavor impartation, thecompound may be added to food and drink or to cosmetics in an amountgenerally within a range of 0.1 ppb to 200 ppm based on the mass of2-(3-benzyloxypropyl)pyridine, preferably 1 ppb to 20 ppm, morepreferably 10 ppb to 2 ppm. By adding the compound thereto within theconcentration range, food and drink or cosmetics can be given a herbal,green or nutty flavor of natural impression.

When the compound represented by the above formula (1) or a salt thereofis diluted alone in water, the resultant aqueous solution providesumami, and the concentration thereof to provide a taste of umami is,based on mass, within a range of 0.01 ppm to 200 pm, but is, forexemplification, preferably within a range of 0.1 ppm to 20 ppm.

However, when combined with an umami ingredient such as salt, sodiumglutamate or the like, or when combined with a volatile umami enhancersuch as 2,4,7-tridecatrienal, 4,7-tridecadienal, trimethylamine,2-methylfuran-3-thiol or the like, the compound or a salt thereofexhibits a synergistic umami and saltiness enhancing effect, and theconcentration of the compound represented by the formula (1) or a saltthereof to exhibit the synergistic effect is, based on the mass of foodand drink, within a range of 0.1 ppb to 40 ppm, preferably 1 ppb to 10ppm, more preferably 5 ppb to 2 ppm.

When combined with a sweet substance such as sucrose or the like, thecompound represented by the formula (1) or a salt thereof exhibits asweetness enhancing effect, and the concentration thereof to exhibit thesynergistic effect is, based on the mass of food and drink, within arange of 0.1 ppb to 40 ppm, preferably 1 ppb to 10 ppm, more preferably5 ppb to 2 ppm.

In particular, when added to a milk or dairy product, a food or drinkproduct containing a milk or dairy product, or a dairy replacementproduct, the compound represented by the formula (1) or a salt thereofof the present invention well exhibits the umami enhancing, saltinessenhancing and sweetness enhancing effect thereof, and gives a feeling ofmilk richness enhancement. The concentration of the compound or a saltthereof to exhibit the effect is, based on the mass of a milk or dairyproduct, a food or drink product containing a milk or dairy product, ora dairy replacement product, within a range of 0.1 ppb to 40 ppm,preferably 1 ppb to 10 ppm, more preferably 5 ppb to 2 ppm.

Examples of umami materials whose umami can be enhanced owing to thesynergistic effect with the compound represented by the formula (1) or asalt thereof of the present invention include inorganic salts such asedible salt, potassium chloride or the like as salty substances; and asumami substances, amino acids such as sodium glutamate, aspartic acid,serine, theanine, arginine, etc., peptides such asdipeptide,oligopeptide, etc., nucleic acids such as inosinic acid, guanylic acid,etc., organic acids such as succinic acid, etc., and arbitrary mixturesthereof, etc.

Examples of sweet materials whose sweetness can be enhanced owing to thesynergistic effect with the compound represented by the formula (1) or asalt thereof of the present invention include sugars such as sucrose,glucose, fructose, maltose, lactose, galactose, maltitose, trehalose,etc.; high intensity sweeteners such as acesulfame K, sucralose,aspartame, neotame, disodium glycyrrhizinate, thaumatin, saccharin and asalt thereof, momordica grosvenori extract, licorice extract,Rebaudioside A, stevia extract, enzyme-processed stevia extract,neohesperidin dihydrochalcone, etc.; sugar alcohols such as xylitol,erythritol, sorbitol, maltitol, palatinit, reduced sugar syrup, etc.;and arbitrary mixtures thereof, etc.

Examples of milks, dairy products, food or drink products containing amilk or dairy product, or dairy replacement products whose richness isespecially enhanced by the compound represented by the formula (1) or asalt thereof of the present invention are mentioned below. Examples ofmilks include raw milk, cow milk, certified milk, partially skimmedmilk, processed milk and others as specified in “Ordinance regardingstandard of element, etc. of milk and dairy products” (Ordinance of theHealth and Welfare Ministry No. 52, Dec. 27, 1951); examples of dairyproducts include cream, butter, butter oil, fermented milk such asyoghurt or the like, lactobacillus beverage, milk beverage, cheese, icecreams, concentrated milk, skimmed concentrated milk, condensed milk,whole milk powder, skimmed milk powder, sweetened milk powder,concentrated whey, whey powder and others as specified in theabove-mentioned Ordinance; examples of food or drink products containinga milk or dairy product include coffee drinks, tea drinks, fruit juicedrinks, carbonated drinks, frozen desserts, Japanese or western-styleconfectionery products, baked goods, soups, curries, stews, variousready-to-serve food and drink products, various snack food products,seasonings such as dressings and the like added with cow milk, cream,butter, cheese, condensed milk, powdered milk and the like; examples ofdairy replacement products include butter replacement products such asmargarine, fast spread and the like to be produced by emulsifying oilsand fats, cream replacement products such as coffee whitener or the liketo be added to coffee, tea or the like, etc.

In the case where the compound represented by the formula (1) or a saltthereof is added to a food or drink product or to a cosmetic product,the compound represented by the formula (1) or a salt thereof itself orone prepared by diluting it may be added to a food or drink product orto a cosmetic product, but apart from this, a flavor compositioncontaining the compound represented by the formula (1) or a salt thereofas an active ingredient may be prepared, and the flavor composition maybe added to a food or drink product or to a cosmetic product to therebymake the food or drink product or the cosmetic product have a flavor. Inaddition, by imparting a flavor to a food or drink product, and byadding the compound represented by the formula (1) or a salt thereof toa flavor composition as an active ingredient therein followed by addingthe flavor composition to the food or drink product, umami of the foodor drink product can be enhanced.

The flavor composition of the present invention may contain the compoundrepresented by the formula (1) or a salt thereof generally in aconcentration of 0.1 ppm to 2% based on the mass of the flavorcomposition, preferably 1 ppm to 0.5%, more preferably 10 ppm to 0.1%.

Further, in the case where the flavor composition is used for impartinga flavor to food and drink or cosmetics, the composition is addedthereto in an amount of approximately 0.01% to 1% so that the additionconcentration of the compound represented by the formula (1) or a saltthereof in the food or drink product or in the cosmetic product could bewithin a range of 0.1 ppb to 200 ppm by mass, preferably 1 ppb to 20ppm, more preferably 10 ppb to 2 ppm. As a result, the compoundrepresented by the formula (1) or a salt thereof can act on the food ordrink product or on the cosmetic product as an active ingredient,thereby imparting a herbal, green, earthy, almond, nutty or rummy flavorof natural impression to the food or drink product or to the cosmeticproduct. Preferably, the compound represented by the formula (1) acts ona food or drink product or on a cosmetic product as an active ingredientto thereby impart a herbal, earthy, almond, nutty or rummy flavor to thefood or drink product or to the cosmetic product.

In the case where the flavor composition is used for enhancing umami,saltiness, sweetness and milk richness of food and drink, thecomposition may be added in an amount of approximately 0.005% to 1% sothat the addition concentration of the compound represented by theformula (1) or a salt thereof to the food or drink product could be,based on the mass of the food or drink product, within a range of 0.1ppb to 40 ppm, preferably 1 ppb to 10 ppm, more preferably 5 ppb to 2ppm. As a result, the compound represented by the formula (1) can act onthe food or drink product as an active ingredient to thereby enhance theumami, saltiness, sweetness or milk richness of the food or drinkproduct.

When the addition concentration of the compound represented by theformula (1) or a salt thereof to food and drink or to cosmetics is lessthan 0.1 ppm, the flavor imparting effect thereof to food and drink orto cosmetics and the umami enhancing effect thereof to food and drinkwould be poor, but when the addition concentration of the compoundrepresented by the formula (1) or a salt thereof to food and drink or tocosmetics is more than 200 ppm, the peculiar flavor of the compounditself would be often unfavorably too strong in food and drink orcosmetics. In addition, there may be an unfavorable probability that thetaste balance of food and drink would be lost.

In the flavor composition, any other generally-usable flavor componentthan the compound represented by the formula (1) or a salt thereof maybe incorporated. The other flavor component that can be incorporated inthe composition along with the compound represented by the formula (1)or a salt thereof includes various synthetic flavors, natural flavors,natural essential oils, animal or vegetable extracts, etc. As the otherflavor components, there may be mentioned synthetic flavors, naturalessential oils, natural flavors, animal or vegetable extracts and othersdescribed in “Japan Patent Office, Glossary of Well-Known ConventionalTechniques (flavors), Part II, Food Flavors, pp. 8-87, published Jan.14, 2000).

Regarding these components, examples of materials for food flavors(flavor compositions and umami-enhancing flavor compositions) include,as hydrocarbon compounds, monoterpenes such as such as α-pinene,β-pinene, myrcene, camphene, limonene, etc., sesquiterpenes such asvalencene, cedrene, caryophyllene, longifolene, etc.,1,3,5-undecatriene, etc.; as alcohol compounds, linear saturatedalkanols such as butanol, pentanol, prenol, hexanol, etc., linearunsaturated alcohols such as (Z)-3-hexen-1-ol, 2,6-nonadienol, etc.,terpene alcohols such as linalool, geraniol, citronellol,tetrahydromyrcenol, farnesol, nerolidol, cedrol, etc., aromatic alcoholssuch as benzyl alcohol, phenylethyl alcohol, furfuryl alcohol, etc.; asaldehyde compounds, linear saturated aldehydes such as acetaldehyde,hexanal, decanal, etc., linear unsaturated aldehydes such as(E)-2-hexenal, 2,4-octadienal, etc., terpene aldehydes such ascitronellal, citral, etc., aromatic aldehydes such as benzaldehyde,cinnamyl aldehyde, vanillin, ethylvanillin, furfural, heliotropine,etc.; as ketone compounds, linear saturated or unsaturated ketones suchas 2-heptanone, 2-undecanone, 1-octen-3-one, etc., linear cyclicdiketones such as acetoin, diacetyl, 2,3-pentadione, maltol,ethylmaltol, 2,5-dimethyl-4-hydroxy-3(2H)-furanone, etc., terpeneketones such as hydroxyketone, carvone, menthene, nootkatone, etc.,ketones derived from terpene degradation products such as α-ionone,β-ionone, β-damascenone, etc., aromatic ketones such as raspberryketone, etc.; as furan/ether compounds, cyclic ether such as rose oxide,linalool oxide, menthofuran, theaspirane, etc.; as ester compounds,aliphatic alcohol acetates such as ethyl acetate, isoamyl acetate, etc.;terpene alcohol acetates such as linalyl acetate, geranyl acetate,lavandulyl acetate, etc., fatty acid lower alcohol esters such as ethylbutyrate, ethyl caproate, etc., aromatic esters such as benzyl acetate,methyl salicylate, etc.; as lactone compounds, saturated lactones suchas γ-decalactone, γ-dodecalactone, δ-decalactone, δ-dodecalactone, etc.,unsaturated lactones such as 7-decen-4-olide, 2-decen-5-olide, etc.; asacid compounds, saturated or unsaturated fatty acids such as butyricacid, octanoic acid, stearic acid, oleic acid, linoleic acid, linolenicacid, etc.; as nitrogen-containing compounds, indole, skatole, pyridine,alkyl-substituted pyradine, methyl anthranilate, etc.: assulfur-containing compounds, methanethiol, dimethyl sulfide, dimethyldisulfide, allyl isothiocyanate, etc. In addition, as various extracts,there are mentioned herb and spice extracts, coffee, green tea, blacktea and oolong tea extracts, milk and milk processed products, andenzymatic decomposition products thereof with lipase, protease, etc.

As materials for umami enhancing flavor compositions, there are furthermentioned amino acids such as sodium glutamate, aspartic acid, etc.,nucleic acids and salts thereof such as inosinic acid, guanylic acid,adenylic acid, uridylic acid, cytidylic acid, etc., yeast extracts,organic acids such as succinic acid, etc., sugars such as ribose,xylose, arabinose, glucose, fructose, rhamnose, lactose, maltose,sucrose, trehalose, cellobiose, maltotriose, starch syrup, etc., inaddition to the above-mentioned materials for food flavors.

Materials for flavors for cosmetics include, in addition to theabove-mentioned food flavors, synthetic flavor compounds such asα-amylcinnamyl aldehyde, dihydrojasmone, methylionone, α-damascone,acetylcedrene, methyl dihydrojasmonate, cyclopentadecanolide, etc.;natural essential oils such as sweet orange, bitter orange, petitgrain,lemon, bergamot, mandarin, neroli, peppermint, spearmint, lavender,chamomile, rosemary, eucalyptus, sage, basil, rose, geranium, jasmine,ylang-ylang, anise, clove, ginger, nutmeg, cardamom, Japanese cedar,Japanese cypress, vetiver, patchouli, labdanum, etc.

In the flavor composition, a fixing agent that is ordinarily used inflavor compositions may be incorporated, as needed. The fixing agentincludes a solvent such as water, ethanol, etc., as well as ethyleneglycol, 1,2-propylene glycol, glycerin, benzyl benzoate, triethylcitrate, Hercolyn, fatty acid triglyceride, fatty acid diglyceride, etc.

Without emulsified, the compound represented by the formula (1) or asalt thereof is, by itself, effective and useful as a flavor modulator,an umami imparting agent, an umami enhancer, a sweetness enhancer, asaltiness enhancer and a milk richness enhancer. By processing thecompound represented by the formula (1) or a salt thereof into anemulsified composition or a powdery composition, the dispersibilitythereof in water can be improved, and the resultant composition can bereadily blended with a food or drink product or with a cosmetic product,and in addition, can change the timing thereof for flavor expression.For example, in the case where the compound represented by the formula(1) or a salt thereof is incorporated in a ramen soup for umamienhancement, and when it is added to an oil-soluble flavor, theoil-soluble flavor will float as oil so that the compound represented bythe formula (1) or a salt thereof contained in oil would act in themouth. On the other hand, when added in the form of an emulsifiedcomposition thereof, fine particles of the compound represented by theformula (1) or a salt thereof could uniformly act in the mouth tothereby realize further strengthened and uniform umami enhancement.

An emulsified composition containing the compound represented by theformula (1) or a salt thereof is not specifically limited, and any oneprepared by emulsifying the compound represented by the formula (1) or asalt thereof in a known method may be employed here. To the compoundrepresented by the formula (1) or a salt thereof, or to a flavorcomposition containing it, water that is a component (B) for use in thepresent invention, one or more selected from sugars, monoalcohols orpolyalcohols that is a component (C), and an emulsifier (D) areincorporated, and for example, the resultant composition is mixed,stirred and emulsified using a homo-mixer, a colloid mill, ahigh-pressure homogenizer or the like to give an emulsified composition.

In emulsifying the above, for example, the compound represented by theformula (1) or a salt thereof is incorporated in an oily phase part, andthe component (B) water, and one or more selected from sugars,monoalcohols or polyalcohols as the component (C) are incorporated in anaqueous phase, and the two may be mixed to prepare an oil-in-wateremulsion.

Water that is the component (B) for use in the present inventionconstitutes the above-mentioned aqueous phase along with the component(C) of sugars, monoalcohols or polyalcohols, and the water content inthe aqueous phase is generally 50% or less, and is especially preferablyin a hydrous state where the content is within a range of about 0 to25%. When the water content is more than 50%, the composition will loseantiseptic performance.

Sugars, monoalcohols or polyalcohols that are the component (C) in thepresent invention are incorporated for stabilizing emulsion. Examples ofsugars include glucose, fructose, sucrose, trehalose, cellobiose,maltotriose, rhamnose, lactose, maltose, ribose, xylose, arabinose,starch syrup, etc.; examples of monoalcohols include ethanol, propanol,isopropanol, etc.; examples of polyalcohols include glycerin, propyleneglycol, 1,3-butylene glycol, sorbitol, maltitol, starch decomposedreduced product, etc.; and a mixture of two or more of these is alsoemployable.

The amount of the aqueous phase to be used in the emulsified compositionis generally within a range of about 1 part by weight to about 10 partsby weight relative to one part by weight of the oily phase part, andespecially preferably within a range of about 1.5 parts by weight toabout 5 parts by weight. As needed, an organic acid such as lactic acid,citric acid, malic acid, tartaric acid or the like may be added to theaqueous phase for the purpose of improving storability.

2-(3-Benzyloxypropyl)pyridine and the above-mentioned various flavorscan dissolve in the component (C) of sugars, monoalcohols orpolyalcohols in a low concentration, and therefore can be incorporatedin the aqueous phase part.

An emulsifier (or a stabilizer as the case may be) of the component (D)for use in the present invention is not specifically limited, andvarious emulsifiers heretofore used in food and drink and others areusable, and examples thereof include fatty acid monoglyceride, fattyacid diglyceride, fatty acid triglyceride, propylene glycol fatty acidester, sucrose fatty acid ester, polyglycerin fatty acid ester,(oxidation-processed) lecithin, processed starch, sorbitan fatty acidester, quillai extract, gum arabic, gum tragacanth, guar gum, karayagum, xanthane gum, pectine, argic acid and salts thereof, carrageenan,gelatin, casein, etc.

One or more emulsifiers (or stabilizer) are incorporated and, forexample, using a homomixer, a colloid mill, a high-pressure homogenizeror the like, the mixture is emulsified to be a form of an emulsifiedflavor preparation. The amount of the emulsifier (or stabilizer) to beused varies depending on the type of the emulsifier (or stabilizer), butfor example, based on the mass of the emulsified flavor preparation, theamount may be within a range of 0.1 to 25% by weight, preferably withina range of 5 to 20% by weight.

Among these emulsifiers, hydrophilic surfactants having HLB of 8 or moreare preferred, and in the case, the emulsifier is mixed in the aqueousphase part. Specifically, there are mentioned polyglycerin fatty acidester, sorbitan fatty acid ester, sucrose fatty acid ester, glycerinfatty acid ester, etc. Examples of polyglycerin fatty acid estersinclude esters of a polyglycerin having a mean polymerization degree of3 or more and a fatty acid having 8 or more carbon atoms, for example,decaglycerin monooleate, decaglycerin monostearate, decaglycerinmonopalmitate, decaglycerin monomyristate and the like having HLB ofabout 8 or more, preferably falling within a range of about 8 to about14. When polyglycerin fatty acid esters having HLB of lower than 8 areused, in general, it is difficult to prepare emulsified particles havinga uniform and small particle size. In addition, the emulsion isunstable, and when it is added to drink, there may be a strong tendencytoward a phenomenon of separation such as precipitation, oil separation,etc.

The content of the polyglycerin fatty acid ester to be contained isgenerally within a range of about 0.05 parts by weight to about 0.5parts by weight relative to 1 part by weight of the oily phase part,preferably within a range of about 0.15 parts by weight to about 0.3parts by weight.

One embodiment of a method for preparation of the emulsified compositionof the present invention is exemplified below. First, the raw materialsfor use for the above-mentioned oily phase part are mixed to prepare onepart by mass of an oily phase part. Apart from this, about 2 to about 50parts by weight (water content, about 0.5 to about 10% by weight) of asolution (aqueous phase) is prepared by mixing and dissolving (B) water,(C) one or more selected from sugars, monoalcohols or polyalcohols, and(D) an emulsifier, and the oily phase part and the aqueous phase partare mixed and emulsified using a homomixer, a colloid mill, ahigh-pressure homogenizer or the like, thereby producing an extremelyfine and stable emulsion of fine particles having a particle size ofabout 0.2 to about 2 μm.

The compound represented by the formula (1) or a salt thereof, or aflavor composition containing it may be contained in the emulsifiedcomposition, generally in an amount of, based on the mass of theemulsified composition, 0.1 ppm to 2%, preferably 1 ppm to 0.5%, morepreferably 10 ppm to 0.1%.

Further, the emulsified composition may be dried to prepare a powderycomposition. For example, an excipient of sugars such as table sugar,lactose, glucose, trehalose, cellobiose, starch syrup, reduced sugarsyrup, etc.; sugar alcohols; various starch decomposed products such asdextrin, etc., as well as starch derivatives, starch, gelatin, naturalgums such as gum arabic and the like is adequately added to thecomposition, and then dried according to an adequate drying method ofspray drying, vacuum drying, freeze drying or the like to give a form ofa powdery composition. The amount of the excipient to be added may beadequately selected depending on the characteristics desired for thepowdery composition.

By adding the compound represented by the formula (1) or a salt thereofof the present invention by itself, or by adding the flavor compositioncontaining the compound represented by the formula (1) or a salt thereofas an active ingredient to food or drink products, herbal, green,earthy, almond, nutty or rummy flavor of natural impression of food anddrink can be enhanced, and additionally, umami, sweetness, saltiness ormilk richness thereof can also be enhanced. Examples of the food ordrink products include carbonated drinks such as cola drink, fruitjuice-added carbonated drink, milk-added carbonated drink, etc.; softdrinks such as fruit juice drink, vegetable drink, isotonic drink, honeydrink, soy milk, vitamin supplement drink, mineral supplement drink,nutrition supplement drink, energy drink, lactobacillus drink, milkdrink, etc.; taste-oriented drinks such as green tea, black tea, oolongtea, herb tea, milk tea, coffee, etc.; alcohol drinks such as shochumixed with soda water, cocktail drink, low-malt beer, fruit liquor,medicinal liquor, etc.; dairy products such as butter, cheese, milk,yoghurt, etc.; desserts such as ice cream, lacto-ice, sherbet, yoghurt,pudding, jelly, dairy dessert, etc., and mixes for producing them;confectionery such as caramel, candy, tablet candy, cracker, biscuit,cookie, pie, chocolate, snack, etc., and mixes such as cake mix and thelike for producing them; general foods such as bread, soup, variousready-to-serve foods, etc.; oral compositions such as tooth paste, etc.

By adding 2-(3-benzyloxypropyl)pyridine that is a preferred embodimentof the present invention to food and drink by itself or as a flavorcomposition containing 2-(3-benzyloxypropyl)pyridine as an activeingredient, herbal, green or nutty flavor of natural impression of foodand drink can be enhanced, or umami can be imparted thereto, or umami,sweetness, saltiness or milk richness thereof can be enhanced. Regardingthe specific examples of the food or drink products in the case, thesame as above shall also apply thereto.

Specific examples of cosmetics whose herbal, earthy, almond, nutty orrummy flavor can be enhanced by adding thereto the compound representedby the formula (1) or a salt thereof of the present invention by itselfor in the form of a flavor composition containing the compoundrepresented by the formula (1) or a salt thereof as an active ingredientinclude perfume; haircare products such as shampoo, hair conditioner,hair cream, pomade, etc.; makeup cosmetics such as face powder, liprouge, etc.; health and hygiene detergents such as face soap, body soap,laundry soap, laundry detergent, sanitizing detergent, deodorantdetergent, etc.; health and hygiene goods such as tooth paste, tissuepaper, toilet paper, etc.; aroma products such as in-room aroma, carcologne, etc.

The same as above shall also apply to specific examples of cosmeticswhose herbal, green or nutty flavor of natural impression can beenhanced by adding thereto, 2-(3-benzyloxypropyl)pyridine that is onepreferred embodiment of the present invention, by itself or in the formof a flavor composition containing 2-(3-benzyloxypropyl)pyridine as anactive ingredient.

The present invention is described more specifically with reference toExamples as hereunder.

EXAMPLES

Reaction crude products and purified product in Examples were analyzedusing the following analytical instruments.

GC measurement: GC-2014 (manufactured by Shimadzu Corporation) andChromatopack C-R8A (manufactured by Shimadzu Corporation)

GC column for GC measurement: TC-1 manufactured by GL Sciences (length30 m, inner diameter 0.53 mm, liquid layer thickness 1.50 μm), TC-1701manufactured by GL Sciences (length 30 m, inner diameter 0.53 mm, liquidlayer thickness 1.00 μm)

GC/MS measurement: 5973 N (manufactured by Agilent Technologies)

GC column for GC/MS measurement: TC-1701 manufactured by GL Sciences(length 30 m, inner diameter 0.25 mm, liquid layer thickness 0.25 μm)

NMR measurement: ECX-400A (manufactured by JEOL Resonance)

Example 1: Preparation of 2-(4-benzyloxybutyl)pyridine

2-(4-Benzyloxybutyl)pyridine is prepared in 5 steps according to thefollowing reaction route.

(1) Preparation of 2-(2-chloroethyl)pyridine

2-Pyridine-ethanol (15.00 g, 122 mmol), triphenyl phosphine (38.40 g,146 mmol) and carbon tetrachloride (100 mL) were put in a 500-mL flask,and heated under reflux. After 1.5 hours, triphenyl phosphine (9.60 g,36.6 mmol) was added thereto and further heated for 30 minutes underreflux.

The reaction liquid was cooled down to room temperature, and thenpentane (200 mL) was added thereto, and filtered using a Kiriyamafunnel. The resultant filtrate was concentrated to give a crude product(17.07 g). This was distilled under reduced pressure to give 11.16 g(yield 65.8%, purity 97.1%) of 2-(2-chloroethyl)pyridine.

(2) Preparation of dimethyl 2-(2-pyridyl)ethylmalonate

2-(2-Chloroethyl)pyridine (10.35 g, 73.1 mmol), N,N-dimethylformamide(100 mL), dimethylmalonate (14.48 g, 110 mmol) and potassium carbonate(18.18 g, 132 mmol) were put in a 300-mL flask, and stirred. After 40minutes, a catalytic amount of sodium iodide (0.25 g) was added thereto,and stirred at 80° C. for 8 hours. Further, dimethyl malonate (9.66 g,73.1 mmol) was added thereto and stirred at 80° C. for 9 hours, at whichthe reaction was stopped.

The reaction liquid was cooled down to room temperature, water with ice(300 g) was added thereto, and this was extracted twice with ether,washed with water (200 g), dried and concentrated to give a crudeproduct (20.9 g). This was distilled under reduced pressure to give 7.78g (yield 44.9%, purity 90.8%) of dimethyl 2-(2-pyridyl)ethylmalonate.

(3) Preparation of methyl 4-(2-pyridyl)butyrate

Dimethyl 2-(2-pyridyl)ethylmalonate (7.72 g, 32.5 mmol), dimethylsulfoxide (270 mL), water (2.34 g, 130 mmol), and sodium chloride (7.60g, 130 mmol) were put in a one-L flask, and stirred at 150° C. for 5.5hours.

The reaction liquid was cooled down to room temperature, and extractedwith water (550 mL) and ether (300 mL) added thereto. Further, water(550 mL) was added, and this was extracted with ether (250 mL). Further,a small amount of sodium bicarbonate and edible salt were added theretountil saturation, and this was extracted with ether (250 mL×3 times).The resultant organic layers were combined, washed with 20% saline water(500 mL), dried with magnesium sulfate, and concentrated to give a crudeproduct (5.17 g, purity 82.2%) of methyl 4-(2-pyridyl)butyrate. Notfurther purified, the crude product was used in the next reaction.

(4) Preparation of 2-pyridine-butanol

In a nitrogen atmosphere, aluminum lithium hydride (0.90 g, 23.7 mmol)and dry ether (20 mL) were put in a 200-mL flask, and stirred at 5° C.in an iced water bath. A dry ether (10 mL) solution of the crude productof methyl 4-(2-pyridyl)butyrate (5.17 g, 28.8 mmol) was dropwise addedthereto at 10° C. or lower, and stirred at the same temperature for 2hours. Further, this was heated up to room temperature and stirred for 3hours.

A saturated aqueous Rochelle salt solution (100 mL) and ether (20 mL)were added thereto, stirred overnight, and the organic layer wasseparated. The aqueous layer was extracted with ether (100 mL), and thecombined organic layers were washed with 20% saline water (100 mL),dried with sodium sulfate and concentrated to give a crude product (3.98g). This was distilled under reduced pressure to give 2.14 g (2-stageyield 44.8%, purity 95.8%) of 2-pyridine-butanol.

(5) Preparation of 2-(4-benzyloxybutyl)pyridine

60% sodium hydride (0.47 g, 11.8 mmol) and dry tetrahydrofuran (5 mL)were put into a 200-mL flask, and stirred in a nitrogen atmosphere. In awater bath, a dry tetrahydrofuran (5 mL) solution of 2-pyridine-butanol(1.50 g, 9.92 mmol) was dropwise added thereto at 25° C. or lower,taking 5 minutes, and then stirred at room temperature for 20 minutes.The reactor was again put in a water bath, and a dry tetrahydrofuran (5mL) solution of benzyl chloride (1.51 g, 11.9 mmol) was dropwise addedthereto at 25° C. or lower, taking 15 minutes, and stirred overnight atroom temperature.

Cold water (5 mL) was added to the reaction liquid for quenching, andthis was extracted with ethyl acetate (30 mL). The resultant organiclayer was washed with 20% saline water (30 mL), dried with sodiumsulfate and concentrated to give a crude product (2.54 g). This waspurified through silica gel chromatography to give 1.04 g (yield 43.4%,purity 98.5%) 2-(4-benzyloxybutyl)pyridine (invention product 1).

Physical Data of 2-(4-benzyloxybutyl)pyridine

¹H NMR (CDCl₃, 400 MHz) δ 1.65-1.73 (m, 2H), 1.79-1.90 (m, 2H),2.78-2.83 (m, 2H), 3.50 (t, 2H, J=6.4 Hz), 4.49 (s, 2H), 7.07-7.11 (m,1H), 7.13 (d, 1H, J=8.0 Hz), 7.24-7.30 (m, 1H), 7.32-7.36 (m, 4H), 7.57(dt, 1H, J=2.0, 7.6 Hz), 8.50-8.53 (m, 1H).

¹³C NMR (CDCl₃, 100 MHz) δ 26.43, 29.40, 38.08, 70.18, 72.87, 120.92,122.73, 127.45, 127.60 (2C), 128.31 (2C), 136.24, 138.57, 149.19,162.04.

MS (EI, 70 eV) m/z 65 (12), 78 (6), 91 (50), 92 (15), 93 (100), 94 (10),106 (84), 107 (17), 117 (8), 118 (8), 120 (30), 132 (6), 134 (52), 135(38), 150 (96), 151 (10).

Example 2: Preparation of 2-(2-phenylethoxyethyl)pyridine

2-(2-Phenylethoxyethyl)pyridine is prepared in a step according to thefollowing reaction route.

60% sodium hydride (17.09 g, 420 mmol) and dry tetrahydrofuran (400 mL)were put in a one-L flask and stirred in a nitrogen atmosphere. In anice bath, a dry tetrahydrofuran (50 mL) solution of 2-phenylethylalcohol (47.48 g, 380 mmol) was dropwise added thereto at 30° C. orlower, taking 20 minutes, and then stirred at room temperature for 10minutes. The reactor was again put in an ice bath, and a drytetrahydrofuran (50 mL) solution of 2-vinylpyridine (49.00 g, 460 mmol)was dropwise added thereto at 30° C. or lower, taking 20 minutes, andheated under reflux for 1.5 hours after the addition.

The reaction liquid was cooled, then cold water (300 mL) was addedthereto for quenching, and this was extracted with ethyl acetate (200mL). The resultant organic layer was washed with 20% saline water (300mL), dried with sodium sulfate and concentrated to give a crude product(139.76 g). This was distilled under reduced pressure to remove a majorpart of the unreacted raw materials, thereby giving a residue (13.13 g)containing the intended product. The residue was purified through silicagel chromatography to give 910 mg (purity 93.9%) of a fractioncontaining the intended, high-purity product. Further, this was purifiedusing a Kugelrohr to give 781 mg (yield 0.9%, purity 98.6%) of2-(2-phenylethoxyethyl)pyridine (invention product 2).

Physical Data of 2-(2-phenylethoxyethyl)pyridine

¹H NMR (CDCl₃, 400 MHz) δ 2.85 (t, 2H, J=6.8 Hz), 3.05 (t, 2H, J=6.4Hz), 3.66 (t, 2H, J=6.8 Hz), 3.83 (t, 2H, J=6.4 Hz), 7.08-7.12 (m, 1H),7.13-7.21 (m, 4H), 7.22-7.28 (m, 2H), 7.55 (dt, 1H, J=2.0, 7.6 Hz),8.50-8.53 (m, 1H).

¹³C NMR (CDCl₃, 100 MHz) δ 36.13, 38.58, 70.06, 71.78, 121.23, 123.57,126.02, 128.20 (2C), 128.83 (2C), 136.17, 138.97, 149.13, 159.20.

MS (EI, 70 eV) m/z 77 (12), 78 (20), 79 (14), 91 (8), 93 (26), 94 (6),104 (54), 105 (30), 106 (100), 107 (44), 122 (89), 123 (12), 136 (21),227 (6).

Example 3: Preparation of

2-[3-(p-methoxybenzyloxy)propyl]pyridine2-[3-(p-methoxybenzyloxy)propyl]pyridine is prepared in a step accordingto the following reaction route.

60% sodium hydride (1.75 g, 43.8 mmol) and dry tetrahydrofuran (10 mL)were put into a 200-mL flask, and stirred in a nitrogen atmosphere. In awater bath, a dry tetrahydrofuran (5 mL) solution of 2-pyridine-propanol(5.00 g, 36.4 mmol) was dropwise added thereto at 30° C. or lower,taking 30 minutes, and then stirred at room temperature for 30 minutes.The reactor was again put in a water bath, and a dry tetrahydrofuran (5mL) solution of p-methoxybenzyl chloride (6.84 g, 43.7 mmol) wasdropwise added thereto at 30° C. or lower, taking 30 minutes, andstirred at room temperature for 5 hours.

Cold water (20 mL) was added to the reaction liquid at 30° C. or lowerfor quenching, and this was extracted with ethyl acetate (50 mL). Theresultant organic layer was washed with 20% saline water (50 mL), driedwith sodium sulfate and concentrated to give a crude product (11.50 g).This was purified through silica gel chromatography to give 5.78 g(yield 61.7%, purity 99.4%) of 2-[3-(p-methoxybenzyloxy)propyl]pyridine(invention product 3).

Physical Data of 2-[3-(p-methoxybenzyloxy)propyl]pyridine

1H NMR (CDCl₃, 400 MHz) δ 2.01-2.08 (m, 2H), 2.86-2.90 (m, 2H), 3.50 (t,2H, J=6.4 Hz), 3.80 (s, 3H), 4.44 (s, 2H), 6.86-6.89 (m, 2H), 7.07-7.14(m, 2H), 7.24-7.28 (m, 2H), 7.56 (dt, 1H, J=1.6, 7.6 Hz), 8.50-8.53 (m,1H).

¹³C NMR (CDCl₃, 100 MHz) δ 29.65, 34.85, 55.24, 69.24, 72.46, 113.71(2C), 120.94, 122.83, 129.21 (2C), 130.63, 136.23, 149.20, 159.07,161.69.

MS (EI, 70 eV) m/z 92 (5), 93 (100), 94 (8), 106 (6), 121 (39), 136(14).

Example 4: Preparation of 2-(2-phenylethylthioethyl)pyridine

2-(2-Phenylethylthioethyl)pyridine is prepared in a step according tothe following reaction route.

2-Vinylpyridine (5.00 g, 47.6 mmol), 2-phenylethane-thiol (6.58 g, 47.6mmol) and ion-exchanged water (21 mL) were put into a 200-mL flask, andstirred at room temperature for 2 days.

The reaction liquid was extracted with ethyl acetate (50 mL), and theresultant organic layer was washed with 20% saline water (50 mL), driedwith sodium sulfate and concentrated to give a crude product (11.37 g).This was purified through silica gel chromatography to give 8.64 g(purity 99.3%) of 2-(2-phenylethylthioethyl)pyridine. A part of this(5.15 g) was further purified using a Kugelrohr to give 5.12 g (yield74.1%, purity 99.9%) of a high-purity product (invention product 4).

Physical Data of 2-(2-phenylethylthioethyl)pyridine

1H NMR (CDCl₃, 400 MHz) δ 2.76-2.82 (m, 2H), 2.84-2.91 (m, 2H),2.94-2.99 (m, 2H), 3.04-3.10 (m, 2H), 7.12-7.23 (m, 5H), 7.26-7.32 (m,2H), 7.61 (dt, 1H, J=1.6, 7.6 Hz), 8.53-8.56 (m, 1H).

¹³C NMR (CDCl₃, 100 MHz) δ 31.72, 33.70, 36.18, 38.40, 121.41, 123.11,126.22, 128.36 (2C), 128.40 (2C), 136.31, 140.47, 149.33, 159.95.

MS (EI, 70 eV) m/z 77 (10), 78 (14), 79 (11), 91 (8), 93 (12), 103 (6),104 (8), 105 (10), 106 (74), 107 (79), 108 (7), 136 (5), 138 (100), 139(31), 140 (9), 152 (9), 215 (14), 243 (6).

Example 5: Preparation of

2-[3-(p-methylbenzyloxy)propyl]pyridine2-[3-(p-methylbenzyloxy)propyl]pyridine is produced in a processaccording to the following reaction route.

60% sodium hydride (1.75 g, 43.8 mmol), and dry tetrahydrofuran (10 mL)were put into a 200-mL flask, and stirred in a nitrogen atmosphere. In awater bath, a dry tetrahydrofuran (5 mL) solution of 2-pyridine-propanol(5.05 g, 36.8 mmol) was dropwise added thereto at 30° C. or lower,taking 30 minutes, and then stirred at room temperature for 30 minutes.The reactor was again put in a water bath, and a dry tetrahydrofuran (5mL) solution of p-methylbenzyl chloride (6.20 g, 44.1 mmol) was dropwiseadded thereto at 30° C. or lower, taking 30 minutes, and stirred at roomtemperature for 2 days.

Cold water (20 mL) was put into the reaction liquid at 30° C. or lowerfor quenching, and this was extracted with ethyl acetate (50 mL). Theresultant organic layer was washed with 20% saline water (50 mL), driedwith sodium sulfate and concentrated to give a crude product (10.13 g).This was purified through silica gel chromatography to give 4.36 g(yield 49.1%, purity 99.7%) of 2-[3-(p-methylbenzyloxy)propyl]pyridine(invention product 5).

Physical Data of 2-[3-(p-methylbenzyloxy)propyl]pyridine

1H NMR (CDCl₃, 400 MHz) δ 2.01-2.09 (m, 2H), 2.34 (s, 3H), 2.86-2.91 (m,2H), 3.51 (t, 2H, J=6.4 Hz), 4.46 (s, 2H), 7.07-7.12 (m, 2H), 7.15 (d,2H, J=8.0 Hz), 7.23 (d, 2H, J=8.0 Hz), 7.56 (dt, 1H, J=2.0, 7.6 Hz),8.50-8.53 (m, 1H).

¹³C NMR (CDCl₃, 100 MHz) δ 21.12, 29.67, 34.86, 69.37, 72.69, 120.94,122.84, 127.72 (2C), 128.98 (2C), 135.47, 136.22, 137.14, 149.21,161.72.

MS (EI, 70 eV) m/z 77 (8), 78 (6), 79 (7), 92 (9), 93 (100), 94 (11),103 (5), 105 (26), 106 (14), 120 (11), 121 (25), 136 (55), 137 (5).

Example 6: Preparation of

2-[3-(2,5-dimethylbenzyloxy)propyl]pyridine2-[3-(2,5-Dimethylbenzyloxy)propyl]pyridine is prepared in a stepaccording to the following reaction route.

60% sodium hydride (1.75 g, 43.8 mmol) and dry tetrahydrofuran (10 mL)were put in a 200-mL flask and stirred in a nitrogen atmosphere. In awater bath, a dry tetrahydrofuran (5 mL) solution of 2-pyridine-propanol(5.00 g, 36.4 mmol) was dropwise added thereto at 35° C. or lower,taking 20 minutes, and then stirred at room temperature for 40 minutes.The reactor was again put in a water bath, and a dry tetrahydrofuran (5mL) solution of 2,5-dimethylbenzyl chloride (6.76 g, 43.7 mmol) wasdropwise added thereto at 30° C. or lower, taking 10 minutes, andstirred at room temperature for 6 hours.

Cold water (30 mL) was added to the reaction liquid at 35° C. or lowerfor quenching, and this was extracted with ethyl acetate (50 mL). Theresultant organic layer was washed with 20% saline water (50 mL), driedwith sodium sulfate and concentrated to give a crude product (12.06 g).This was purified through silica gel chromatography to give 5.62 g(yield 60.5%, purity 99.1%) of2-[3-(2,5-dimethylbenzyloxy)propyl]pyridine (invention product 6).

Physical Data of 2-[3-(2,5-dimethylbenzyloxy)propyl]pyridine

1H NMR (CDCl₃, 400 MHz) δ 2.03-2.11 (m, 2H), 2.29 (s, 3H), 2.31 (s, 3H),2.86-2.92 (m, 2H), 3.55 (t, 2H, J=6.4 Hz), 4.46 (s, 2H), 6.98-7.14 (m,5H), 7.56 (dt, 1H, J=1.6, 7.6 Hz), 8.51-8.53 (m, 1H).

¹³C NMR (CDCl₃, 100 MHz) δ 18.30, 20.92, 29.71, 34.91, 69.74, 71.30,120.96, 122.85, 128.27, 129.25, 130.07, 133.37, 135.12, 136.12, 136.25,149.20, 161.70.

MS (EI, 70 eV) m/z 91 (9), 92 (7), 93 (100), 94 (8), 106 (9), 117 (11),118 (36), 119 (20), 120 (10), 121 (26), 136 (38), 196 (8).

Comparative Example 1: Preparation of 2-(2-benzyloxyethyl)pyridine

An aqueous 25 wt % sodium hydroxide solution (120.0 g, 750 mmol),2-pyridine-ethanol (12.34 g, 100 mmol), benzyl chloride (15.51 g, 123mmol) and tetra-n-butylammonium bromide (1.61 g, 4.99 mmol) were putinto a 300-mL flask, stirred at 45° C. for 3 hours, and the reactionliquid was extracted with hexane (100 mL). The organic layer was washedwith 20% saline water (100 mL), and the product was formed into ahydrochloride thereof with 2 mol/L hydrochloric acid (100 mL) andextracted in an aqueous layer, and then an aqueous saturated sodiumcarbonate solution (150 mL) was added to the aqueous layer to make italkaline. The aqueous layer containing the intended product wasextracted with ethyl acetate (100 mL×once, 50 mL×once). The resultantorganic layers were combined, washed with 20% saline water (100 mL), theorganic layer was dewatered and dried with anhydrous sodium sulfate,ethyl acetate was recovered under reduced pressure to give aconcentrated product (22.75 g). The concentrated product was purifiedthrough distillation under reduced pressure to give2-(2-benzyloxyethyl)pyridine (16.51 g, yield 77.4%, purity 99.9%)(comparative product 1).

Physical Data of 2-(2-benzyloxyethyl)pyridine

1H NMR (400 MHz, CDCl₃) δ 3.11 (t, 2H, J=6.8 Hz), 3.86 (t, 2H, J=6.8Hz), 4.53 (s, 2H), 7.12 (dd, 1H, J=7.6, 5.2 Hz), 7.22 (d, 1H, J=7.6 Hz),7.24-7.33 (m, 5H), 7.60 (dt, 1H, J=1.2, 7.6 Hz), 8.53 (dm, 1H, J=5.2Hz).

¹³C NMR (100 MHz, CDCl₃) δ 38.71, 69.59, 72.95, 121.31, 123.59, 127.50,127.58 (2C), 128.31 (2C), 136.23, 138.35, 149.26, 159.20.

MS (EI, 70 eV) m/z 39 (10), 51 (12), 65 (27), 78 (12), 79 (13), 91 (75),92 (10), 93 (24), 106 (61), 107 (100), 122 (71), 168 (2), 182 (6).

Example 7: Evaluation of Flavor of Invention Products 1 to 6

A 1% ethanol solution of the invention products 1 to 6 prepared inExamples 1 to 6 was prepared as an evaluation solution. The evaluationsolution was prepared in a sample bottle. Regarding the flavor of thesample smelling from the bottle mouth and the flavor of a flavor paperprepared by infiltrating the evaluation solution into a paper,well-trained 5 panelists tested the solution for flavor evaluation. Atypical evaluation of each product is shown in Table 1.

TABLE 1 Compound Flavor Evaluation 2-(4-benzyloxybutyl)pyridine Earthy(invention product 1) 2-(2-phenylethoxyethyl)pyridine Earthy,hyacinthine (invention product 2)2-[3-(p-methoxybenzyloxy)propyl]pyridine Bitter almond (inventionproduct 3) 2-(2-phenylethylthioethyl)pyridine Metallic spicy savor(invention product 4) 2-[3-(p-methylbenzyloxy)Propyl]pyridine Nutty(invention product 5) 2-[3-(2,5-dimethylbenzyloxy)propyl]pyridine Rummy(invention product 6)

Example 8: Pineapple-Like Compounded Flavor Composition

According to the formulation of the following Table 2, a pineapple-likecompounded flavor composition was formulated to be a comparative product2.

TABLE 2 Ethyl acetate 12 part by mass Ethyl butyrate 10 ″ Isoamylacetate 4 ″ Isoamyl valerate 2.2 ″ Isobutyric acid 2.8 ″ Isovaleric acid1.2 ″ Allyl caproate 1.4 ″ Ethyl caproate 0.8 ″ Ethyl caprylate 0.6 ″Ethyl caprate 0.8 ″ Isoamyl alcohol 1.4 ″ Diethyl malonate 1.2 ″ Citral0.6 ″ Linalool 0.2 ″ Maltol 0.8 ″ Propylene glycol 500 ″ 95% ethanol 460″ Total 1000

0.2 g (0.02% by mass) of any of the invention products 1 to 6 was mixedin 999.8 g of the above-mentioned, pineapple-like compounded flavorcomposition (comparative product 2) to prepare a novel pineapple-likecompounded flavor composition. One prepared by mixing the inventionproduct 1 in the comparative product 2 was referred to as an inventionproduct 7, one prepared by mixing the invention product 2 in thecomparative product 2 was referred to as an invention product 8, oneprepared by mixing the invention product 3 in the comparative product 2was referred to as an invention product 9, one prepared by mixing theinvention product 4 in the comparative product 2 was referred to as aninvention product 10, one prepared by mixing the invention product 5 inthe comparative product 2 was referred to as an invention product 11,and one prepared by mixing the invention product 6 in the comparativeproduct 2 was referred to as an invention product 12. Five expertpanelists compared the invention products 7 to 12 with the comparativeproduct 2. For flavor evaluation, 10 ml of the flavor composition wasprepared in a sample bottle (30 ml). Well-trained five panelistsevaluated the flavor smelling from the bottle mouth and the flavor ofthe flavor paper prepared by infiltrating the flavor composition into apaper. As a result, all of the five expert panelists concluded that theinvention products 7 to 12 all had fresher and better pineapplecharacteristics of natural impression than the comparative product 2 andwere all remarkably more excellent than the latter in point of theflavor durability.

Example 9: Incorporation of Pineapple-Like Compounded Flavor Compositionin Sherbet

The pineapple-like compounded flavor composition (comparative product 2or invention product 7) obtained in Example 8 was added to sherbethaving the following formulation to prepare sherbet according to anordinary method, and well-trained 5 panelists ate it for organolepticevaluation.

Sherbet Compounding Formulation (Part by Mass)

Sugar: 10, starch syrup (75%): 6, fructose sucrose liquid sugar syrup(75%): 5, citric acid (crystal): 0.1, 20% pineapple juice: 10, inventionproduct 7 (or comparative product 2): 0.2, water to make a total amountof 100.

Five panelists ate these sherbet products for organoleptic evaluation.As a result, all the five panelists concluded that the sherbet addedwith the invention product 7 had fresher and better pineapplecharacteristics of natural impression than the sherbet added withcomparative product 2, and evaluated that, regarding the taste thereof,the former realized better umami and sweetness than the latter.

Example 10: Lilac-Type Compounded Flavor Composition

According to the formulation of the following Table 3, a lilac-typecompounded flavor composition was prepared to be a comparative product3.

TABLE 3 Phenylethyl acetate 4 part by mass Cinnamic alcohol 16 ″Terpineol 52 ″ Cyclamen aldehyde 4 ″ Heliotropine 20 ″ Cinnamyl acetate4 ″ Carnation absolute 8 ″ Linalool 12 ″ Indole 0.8 ″ Styrax resinoid 12″ Ylang-ylang 4 ″ Hydroxycitronellal 116 ″ Benzyl acetate 8 ″Anisaldehyde 8 ″ Absolute jasmine 8 ″ Phenylethyl alcohol 111.2 ″ Anisealcohol 12 ″ 1,3-butylene glycol 600 ″ Total 1000

0.2 g (1% by mass) of any of the invention products 1 to 6 was mixed in99.8 g of the above-mentioned lilac-type flavor composition (comparativeproduct 3) to prepare a novel lilac-type compounded flavor composition.One prepared by mixing the invention product 1 in the comparativeproduct 3 was referred to as an invention product 13; one prepared bymixing the invention product 2 in the comparative product 3 was referredto as an invention product 14; one prepared by mixing the inventionproduct 3 in the comparative product 3 was referred to as an inventionproduct 15; one prepared by mixing the invention product 4 in thecomparative product 3 was referred to as an invention product 16; oneprepared by mixing the invention product 5 in the comparative product 3was referred to as an invention product 17; one prepared by mixing theinvention product 6 in the comparative product 3 was referred to as aninvention product 18. Five panelists compared the invention products 13to 18 with the comparative product 3. As a result, all the panelistsconcluded that the invention products 13 to 18 all had fresher lilaccharacteristics of natural impression than the comparative product 3 andwere all remarkably more excellent than the latter in point of theflavor durability.

Example 11: Incorporation of Lilac-Type Compounded Flavor Composition inShampoo

The lilac-type compounded flavor composition (comparative product 3 orinvention product 13) obtained in Example 10 was added to shampoo havingthe following formulation to prepare shampoo according to an ordinarymethod, and well-trained 5 panelists tried it in shampooing fororganoleptic evaluation.

Shampoo Formulation (Part by Mass)

Sodium polyoxyethylene laurylsulfate: 20, coconut oil fatty aciddiethanolamide: 5, glycerin: 4, invention product 13 (or comparativeproduct 3); 0.2, water to make a total amount of 100.

Five panelists tested these shampoo products for organolepticevaluation. As a result, all the five panelists concluded that theshampoo added with the invention product 13 had fresher and better lilaccharacteristics of natural impression than the shampoo added with thecomparative product 3.

Example 12: Confirmation of Umami

A solution was prepared by dissolving any of the invention products 1 to6 in water to have a concentration shown in Table 4. As a comparativeproduct, a solution was prepared by dissolving the comparative product 1(2-(2-benzyloxyethyl)pyridine) to have the same concentration. Waterwith no addition was prepared as a control product. Well-trained 10panelists tasted the solutions prepared by dissolving any the inventionproducts 1 to 6 and the comparative product 1 for organolepticevaluation of umami.

Umami evaluation was based on the control product of water. Each samplewas given any of a point 0, no difference from control; 1, somewhatstronger than control; 2, stronger than control; 3, considerablystronger than control; and 4, poor taste balance. An average point givenby those 10 panelists is shown in Table 4.

TABLE 4 Addition Invention Invention Invention Invention InventionInvention Comparative Concentration Product 1 Product 2 Product 3Product 4 Product 5 Product 6 Product 1   2 ppb 0.0 0.0 0.0 0.0 0.0 0.00.0  10 ppb 0.8 0.7 0.8 0.7 0.6 0.5 0.1   0.1 ppm 1.6 1.5 1.4 1.6 1.41.2 0.8   1 ppm 2.3 2.0 2.1 2.2 2.0 2.0 1.5  20 ppm 2.9 2.8 2.8 3.0 2.72.6 2.2  200 ppm 3.4 3.2 3.0 3.6 3.1 3.0 2.8  500 ppm 3.8 3.8 3.6 3.93.6 3.6 3.3 2000 ppm 4.0 4.0 3.9 4.0 3.9 3.9 3.8

As shown in Table 4, the aqueous solutions prepared by dissolving any ofthe invention products 1 to 6 alone in water had umami. It is known thatthe solutions provided umami when the concentration of the producttherein fell within a range of 0.01 ppm to 200 ppm by mass, and inparticular, provided good umami when the concentration was 0.1 ppm to 20ppm or so.

On the other hand, the aqueous solution prepared by dissolving thecomparative product 1 alone in water also had umami. It is known thatthe solution provided umami when the concentration fell within a rangeof 0.1 ppm to 2000 ppm by mass, and in particular, provided good umamiwhen the concentration was 1 ppm to 200 ppm or so.

Specifically, it is recognized that the umami imparting effect of theinvention products 1 to 6 is stronger by 10 times or so than thecomparative product 1, and the concentration of the invention products 1to 6 to provide the same umami intensity was about 1/10 that of thecomparative product 1.

Example 13: Confirmation of Umami Imparting and Saltiness EnhancingEffect

An aqueous 0.3 mass % sodium chloride solution (control), and solutionsof the invention products 1 to 6 each dissolved in a 0.3 mass % sodiumchloride solution to have the concentration shown in Table 5 wereprepared. As a comparative product, a solution was prepared bydissolving the comparative product 1 in 0.3 mass % sodium chloride.Well-trained 10 panelists tasted the solutions for organolepticevaluation of umami impartment and saltiness enhancement.

Umami and saltiness scores are as follows, based on the aqueous 0.3 mass% sodium chloride solution as a control. Each sample was given any of apoint 0, no change from control; 1, slightly higher umami and saltinessthan control; 2, higher umami and saltiness than control; 3,considerably higher umami and saltiness than control; 4, extremelyhigher umami and saltiness than control; and 5, bitter as lackingbalance of umami and saltiness. An average point given by those 10panelists is shown in Table 5.

TABLE 5 Addition Invention Invention Invention Invention InventionInvention Comparative Concentration Product 1 Product 2 Product 3Product 4 Product 5 Product 6 Product 1 0.05 ppb 0.0 0.0 0.0 0.0 0.0 0.00.0  0.1 ppb 0.8 0.7 0.8 0.6 0.8 0.5 0.0   1 ppb 1.4 1.5 1.6 1.8 1.5 1.30.6   10 ppb 2.3 2.4 2.6 2.3 2.2 2.0 1.5  0.1 ppm 3.2 3.0 3.3 3.4 3.02.9 2.1  0.5 ppm 3.7 3.9 3.5 3.8 3.6 3.5 3.0   2 ppm 4.3 4.4 4.2 4.5 4.24.1 3.4   10 ppm 4.7 4.6 4.8 4.8 4.6 4.6 4.2   50 ppm 4.9 5.0 4.9 5.04.8 4.8 4.8

As shown in Table 5, the aqueous solutions prepared by dissolving any ofthe invention products 1 to 6 in an aqueous 0.3 mass % sodium chloridesolution had umami and salty taste, and they provided umami at a lowerconcentration than that of the solutions prepared by dissolving theinvention products 1 to 6 in water in Example 12. Accordingly, theconcentration of the invention products 1 to 6 capable of realizingumami impartation and saltiness enhancement when combined with ediblesalt is considered to be within a range of 0.1 ppb to 2 ppm by mass,preferably 1 ppb to 0.5 ppm. In addition, it is recognized that theumami imparting effect of the invention products 1 to 6 is higher byabout 10 times than that of the comparative product 1, and theconcentration of the invention products 1 to 6 to realize the samedegree of umami intensity is about 1/10 that of the comparative compound1.

Example 14: Confirmation of Umami and Saltiness Enhancement

Well-trained 5 panelists tasted an aqueous solution of 0.3 mass % ediblesalt and 0.03 mass % sodium glutamate (MSG), and aqueous solutionsprepared by adding to the aqueous solution, 10 ppb of any of theinvention products 1 to 6, for organoleptic evaluation in point of umamiand saltiness enhancement. As a result, all the five panelists concludedthat the aqueous solutions added with the invention products 1 to 6 gavestronger umami and saltiness than the aqueous solution of 0.3 mass %edible salt and 0.03 mass % sodium glutamate (MSG).

Example 15: Confirmation of Umami Enhancing Effect

Well-trained 5 panelists tasted an aqueous solution of 0.1 mass % sodiuminosinate (5′-IMP.2Na), and aqueous solutions prepared by adding to theaqueous 0.1 mass % sodium inosinate solution, 10 ppb of any of theinvention products 1 to 6, for organoleptic evaluation in point ofumami. As a result, all the five panelists concluded that the aqueoussolutions added with 10 ppb of the invention products 1 to 6 gavestronger umami than the aqueous 0.1 mass % sodium inosinate solution.

Example 16: Confirmation of Sweetness Enhancing Effect

Well-trained 5 panelists tasted an aqueous 3 mass % sucrose solution,and aqueous solutions prepared by adding to the aqueous 3 mass % sucrosesolution, 5 ppb of any of the invention products 1 to 6, fororganoleptic evaluation in point of sweetness. As a result, all the fivepanelists concluded that the aqueous solutions added with 5 ppb of theinvention products 1 to 6 gave stronger sweetness than the aqueous 3mass % sucrose solution.

Example 17: Addition to Soup Broth for Udon Noodle

0.05 ppm of any of the invention products 1 to 6 was added tocommercially-available soup broth for udon noodle (tripe strength). 200ml of hot water was added to 100 ml of each of the added soup broth andthe non-added soup broth, and well-trained 5 panelists tasted them fororganoleptic evaluation in point of umami. As a result, all the fivepanelists concluded that the soup broth added with 0.05 ppm of theinvention products 1 to 6 provided stronger umami, saltiness andsweetness than the non-added, commercial soup broth.

Example 18: Addition of Katsuobushi-Like Compounded Flavor Compositionto Mentsuyu (Soup Broth for Noodle)

According to the formulation of the following Table 6, akatsuobushi-like compounded flavor composition (a type that impartsumami in addition to flavor) was prepared.

TABLE 6 1,2,3-trimethoxy-5-methylbenzene 40 part by mass Isosafrole 2 ″2-penten-1-ol 8 ″ Trans-2-pentenal 1 ″ Cyclotene 10 ″ Diacetyl 5 ″2-methylfuran 20 ″ Acetic acid 3 ″ γ-butyrolactone 1 ″(E,Z,Z)-2,4,7-tridecatrienal 0.00005 ″ 4,7-tridecadienal 0.00005 ″Trimethylamine 0.00001 ″ 2-methylfuran-3-thiol 0.00005 ″2-(4-benzyloxybutyl)pyridine 1 ″ (invention product 1) 95% ethanol 100 ″Propylene glycol balance ″ Total 1000

According to the formulation of the following Table 7, mentsuyu wasprepared, and 0.02% of the katsuobushi-like compounded flavorcomposition of Table 6 was added thereto.

TABLE 7 Soy sauce 500 Part by mass Mirin (sweet cooking rice wine) 200 ″Sugar 100 ″ Yeast extract 6 ″ Water 194 ″ Total 1000

Well-trained 5 panelists tasted the mentsuyu not added with thekatsuobushi-like compounded flavor composition and the katsuobushi-likecompounded flavor composition-added mentsuyu for organolepticevaluation. As a result, all the five panelists concluded that thementsuyu added with the katsuobushi-like compounded flavor compositioncontaining the invention product 1 was better as given akatsuobushi-like flavor than the non-added mentsuyu, additionally sayingthat the former was better as given enhanced umami, saltiness andsweetness.

Example 19: Katsuobushi-Like Emulsified Flavor Composition

100 g of the katsuobushi-like compounded flavor composition of Table 6as an oily phase, and a solution of 312.5 g of glycerin, 65 g ofion-exchanged water and 22.5 g of decaglycerin monostearate as anaqueous phase were prepared. The two were mixed by stirring with aTK-homogenizer (manufactured by Primix Corporation) at 8000 rpm for 10minutes for emulsification. Thus, a katsuobushi-like emulsified flavorcomposition in the form of an O/W emulsion was prepared, whoseabsorbance at a wavelength 680 nm in 1/2000 dilution with ion-exchangedwater was 0.2 Abs. This is an invention product 19 (having a2-(4-benzyloxybutyl)pyridine concentration of 0.2% by mass).

Example 20: Addition of Katsuobushi-Like Emulsified Flavor Compositionto Mentsuyu

Mentsuyu was prepared according to the formulation of the above Table 7,and 0.01% of the invention product 19, katsuobushi-like emulsifiedflavor composition was added thereto (2-(4-benzyloxybutyl)pyridineconcentration 0.2 ppm).

Well-trained 5 panelists tasted the mentsuyu not added with thekatsuobushi-like emulsified flavor composition and the katsuobushi-likeemulsified flavor composition-added mentsuyu for organolepticevaluation. As a result, all the five panelists concluded that thementsuyu added with the katsuobushi-like emulsified flavor compositionof the invention product 19 was better as given a katsuobushi-likeflavor, additionally saying that the composition-added mentsuyu was anextremely better-tasting one as given greatly enhanced umami, saltinessand sweetness.

Example 21: Katsuobushi-Like Powdery Flavor Composition

70 g of gum arabic and 20 g of trehalose were dissolved in 150 g ofwater to be an aqueous phase, sterilized by heating at 85 to 90° C. for15 minutes, and then cooled down to 40° C. As an oily phase, 10 g of thekatsuobushi-like compounded flavor composition of Table 6 was addedthereto and mixed, and then emulsified with a TK-homomixer to give anO/W emulsified composition. The emulsified composition was spray-dried,using a mobile minor spray drier by Niro, at an inlet temperature of140° C. and an outlet temperature of 75° C. to produce 95 g of akatsuobushi-like powdery flavor composition (invention product 20:2-(4-benzyloxybutyl)pyridine concentration 0.1% by mass).

Example 22: Addition of Katsuobushi-Like Powdery Flavor Composition toPowdery Ramen Soup

Powdery ramen soup was prepared according to the formulation of Table 8.1% by mass of the invention product 20 was further added thereto.

TABLE 8 Amount Added (part by mass) Edible salt 360 Powdered soy sauce220 Sodium L-glutamate 120 Meat extract powder 100 Sugar 80 Seafoodextract powder 30 Vegetable extract powder 20 Spice powder 10 Sodiumsuccinate 5 Dextrin 55 Total 1000

Powdery ramen soup added with the katsuobushi-like powdery flavorcomposition of the invention product 20 and that not added with it wereprepared each in an amount of 10 g, 600 ml/one of hot water (70° C.) wasadded to dilute them, and well-trained 5 panelists tasted them fororganoleptic evaluation. As a result, all the five panelists concludedthat the ramen soup added with the katsuobushi-like powdery flavorcomposition of the invention product 20 was better as given akatsuobushi-like flavor, additionally saying that the composition-addedramen soup was an extremely better-tasting one as given greatly enhancedumami, saltiness and sweetness.

Example 23: Milk-Like Compounded Flavor Composition (a Type that ImpartsRichness in Addition to Flavor)

According to the formulation of the following Table 9, a milk-likecompounded flavor composition (comparative product 4) was prepared.

TABLE 9 Vanillin 25.0 part by mass Ethylvanillin 35.0 ″ Maple lactone2.5 ″ Ethylmaltol 3.5 ″ γ-undecalactone 2.0 ″ γ-nonalactone 10.0 ″δ-decalactone 2.5 ″ Acetylmethylcarbinol 3.0 ″ Diacetyl 7.0 ″ Butyricacid 5.0 ″ Propylene glycol 904.5 ″ Total 1000.0 ″

One mg (10 ppm) of any of the invention products 1 to 6 was mixed in 100g of the milk-like compounded flavor composition (comparative product 4)to prepare a novel milk-like compounded flavor composition. One preparedby mixing the invention product 1 in the comparative product 4 wasreferred to as a milk-like compounded flavor composition of an inventionproduct 21; one prepared by mixing the invention product 2 in thecomparative product 4 was referred to as that of an invention product22; one prepared by mixing the invention product 3 in the comparativeproduct 4 was referred to as that of an invention product 23; oneprepared by mixing the invention product 4 in the comparative product 4was referred to as that of an invention product 24; one prepared bymixing the invention product 5 in the comparative product 4 was referredto as that of a milk-like compounded flavor composition of an inventionproduct 25; and one prepared by mixing the invention product 6 in thecomparative product 4 was referred to as that of an invention product26.

Example 24: Addition to Aqueous Solution of Skim Milk

A mixed solution (aqueous solution of skin milk) of 10 parts by mass ofcommercial skim milk and 90 parts by mass of water was prepared, and0.1% of the milk-like compounded flavor composition prepared in Example23 was added thereto. Well-trained 5 panelists tasted the aqueoussolution of skim milk not added with the milk-like compounded flavorcomposition, and the aqueous solution of skim milk added with 0.1% bymass of any of the comparative product 4 and the invention products 21to 26 for organoleptic evaluation. As a result, all the five panelistsconcluded that the aqueous solution of skim milk added with thecomparative product 4 was better-tasting than the non-added aqueoussolution of skim milk as given enriched milk flavor, further saying thatthe aqueous solutions of skim milk added with any of the inventionproducts 21 to 26 were as a whole extremely better than the aqueoussolution of skim milk added with the comparative product 4 as givenstronger umami and sweetness and further given stronger milk richness,that is, the taste of the former was extremely good as a whole.

Example 25: Milk-Like Emulsified Flavor Composition

According to the formulation of the following Table 10, milk-likecompounded flavor compositions (reference products 1 to 7) wereprepared.

TABLE 10 Milk-like Compounded Flavor Composition (part by mass)Reference Reference Reference Reference Reference Reference ReferenceProduct 1 Product 2 Product 3 Product 4 Product 5 Product 6 Product 7Vanillin 25.0 25.0 25.0 25.0 25.0 25.0 25.0 Ethylvanillin 35.0 35.0 35.035.0 35.0 35.0 35.0 Maple lactone 2.5 2.5 2.5 2.5 2.5 2.5 2.5 Ethylmaltol 3.5 3.5 3.5 3.5 3.5 3.5 3.5 γ-undecalactone 2.0 2.0 2.0 2.0 2.02.0 2.0 γ-nonalactone 10.0 10.0 10.0 10.0 10.0 10.0 10.0 δ-decalactone2.5 2.5 2.5 2.5 2.5 2.5 2.5 Acetylmethylcarbinol 3.0 3.0 3.0 3.0 3.0 3.03.0 Diacetyl 7.0 7.0 7.0 7.0 7.0 7.0 7.0 Butyric acid 5.0 5.0 5.0 5.05.0 5.0 5.0 Invention product 1 — 10.0 — — — — — Invention product 2 — —10.0 — — — — Invention product 3 — — — 10.0 — — — Invention product 4 —— — — 10.0 — — Invention product 5 — — — — — 10.0 — Invention product 6— — — — — — 10.0 Middle chain fatty acid balance balance balance balancebalance balance balance triglyceride Total 1000.0 1000.0 1000.0 1000.01000.0 1000.0 1000.0

100 g of any of the milk-like compounded flavor compositions (referenceproducts 1 to 7) of Table 10 as an oily phase, and a solution of 312.5 gof glycerin, 65 g of ion-exchanged water and 22.5 g of decaglycerinmonopalmitate as an aqueous phase were prepared. The two liquids weremixed by stirring with a TK-homogenizer (manufactured by PrimixCorporation) at 8000 rpm for 10 minutes for emulsification. Thus, amilk-like emulsified flavor composition in the form of an O/W emulsionwas prepared, whose absorbance at a wavelength 680 nm in 1/2000 dilutionwith ion-exchanged water was 0.2 Abs. One prepared by emulsifying thereference product 1 was referred to as a milk-like emulsified flavorcomposition of a comparative product 5, one prepared by emulsifying thereference product 2 was referred to as that of an invention product 27,one prepared by emulsifying the reference product 3 was referred to asthat of an invention product 28, one prepared by emulsifying thereference product 4 was referred to as that of an invention product 29,one prepared by emulsifying the reference product 5 was referred to asthat of an invention product 30, one prepared by emulsifying thereference product 6 was referred to as that of an invention product 31,and one prepared by emulsifying the reference product 7 was referred toas that of an invention product 32.

Example 26: Addition of Milk-Like Emulsified Flavor Composition toLacto-Ice

According to the formulation of the following Table 11, lacto-ice wasprepared, and 0.01% of the milk-like compounded flavor composition ofthe invention products 27 to 32 or the comparative product 5 was addedthereto. For preparing lacto-ice, all the materials were dissolved byheating and emulsified with a homogenizer at 150 kg/cm², and then agedovernight at 10° C. This was frozen with a freezer, and then hardened upat −40° C. for 1 hour to give lacto-ice.

TABLE 11 Sweetened condensed milk 4 Part by mass Skim milk 7 ″ Vegetableoil and fat 9 ″ Sugar 10 ″ Egg yolk 12.5 ″ Stabilizer 0.3 ″ Emulsifier0.4 ″ Vanilla flavor 0.1 ″ Water balance ″ Total 100 ″

Well-trained 5 panelists tasted the lacto-ice added with the milk-likeemulsified flavor composition of the invention products 27 to 32 or thecomparative product 5, and the non-added lacto-ice for organolepticevaluation. As a result, all the five panelists first concluded that thelacto-ice added with the comparative product 5 provided better milk-likeflavor than the lacto-ice not added with the flavor. Further, all thefive panelists concluded that the lacto-ice added with any of theinvention products 27 to 32 provided better milk-like flavor than thelacto-ice added with the comparative product 5 and that, regardingtaste, the former provided enhanced umami, sweetness and milk richnessand were all extremely delicious and good.

Example 27: Milk-Like Powdery Flavor Composition

As an aqueous phase, 70 g of gum arabic and 20 g of trehalose weredissolved in 150 g of water, and sterilized by heating at 85 to 90° C.for 15 minutes, and then cooled down to 40° C. As an oily phase, 10 g ofthe reference product 2 was added thereto and mixed, and then emulsifiedwith a TK-homogenizer to produce an O/W emulsified composition. Theemulsified composition was spray-dried, using a mobile minor spray drierby Niro, at an inlet temperature of 140° C. and an outlet temperature of75° C. to produce 95 g of a milk-like powdery flavor composition(invention product 33: 2-(4-benzyloxybutyl)pyridine concentration 0.1%by mass).

Example 28: Addition to Aqueous Solution of Skim Milk

Skim milk, and a mixture of 99 parts by mass of skim milk and 1 part bymass of the invention product 33 were prepared by thorough mixing. 10parts by mass of the skim milk or the mixture of skim milk and theinvention product 33 was mixed with 90 parts by mass of water to preparea mixture solution (aqueous solution of skim milk). Well-trained 5panelists tasted these for organoleptic evaluation. As a result, all thefive panelists concluded that the aqueous solution of skim milk addedwith the invention product 33 was better than the non-added aqueoussolution of skim milk in that the former provided stronger milky flavor,stronger umami and sweetness, and stronger milk richness, namely, theformer had an extremely good milky taste.

Example 29: Pineapple-Like Emulsified Flavor Composition

According to the formulation of the following Table 12, a pineapple-likecompounded flavor composition was prepared (reference products 8 to 13).

TABLE 12 Formulation of Pineapple-like Compounded Flavor (part by mass)Reference Reference Reference Reference Reference Reference Product 8Product 9 Product 10 Product 11 Product 12 Product 13 Ethyl acetate 1212 12 12 12 12 Ethyl butyrate 10 10 10 10 10 10 Isoamyl acetate 4 4 4 44 4 Isoamyl valerate 2.2 2.2 2.2 2.2 2.2 2.2 Isobutyric acid 2.8 2.8 2.82.8 2.8 2.8 Isovaleric acid 1.2 1.2 1.2 1.2 1.2 1.2 Allyl caproate 1.41.4 1.4 1.4 1.4 1.4 Ethyl caproate 0.8 0.8 0.8 0.8 0.8 0.8 Ethylcaprylate 0.6 0.6 0.6 0.6 0.6 0.6 Ethyl caprate 0.8 0.8 0.8 0.8 0.8 0.8Isoamyl alcohol 1.4 1.4 1.4 1.4 1.4 1.4 Diethyl malonate 1.2 1.2 1.2 1.21.2 1.2 Citral 0.6 0.6 0.6 0.6 0.6 0.6 Linalool 0.2 0.2 0.2 0.2 0.2 0.2Maltol 0.8 0.8 0.8 0.8 0.8 0.8 Invention product 1 0.2 — — — — —Invention product 2 — 0.2 — — — — Invention product 3 — — 0.2 — — —Invention product 4 — — — 0.2 — — Invention product 5 — — — — 0.2 —Invention product 6 — — — — — 0.2 Middle chain fatty acid balancebalance balance balance balance balance triglyceride total 1000 10001000 1000 1000 1000

As an oily phase, 100 g of the pineapple-like compounded flavorcomposition of Table 12 (reference products 8 to 13), and as an aqueousphase, 312.5 g of glycerin and 22.5 g of decaglycerin monooleatedissolved in 65 g of ion-exchanged water were prepared, and the twoliquids were mixed by stirring with a TK-homogenizer (manufactured byPrimix Corporation) at 8000 rpm for 10 minutes for emulsification. Thus,a pineapple-like emulsified flavor composition in the form of an O/Wemulsion was prepared, whose absorbance at a wavelength 680 nm in 1/2000dilution with ion-exchanged water was 0.2 Abs. One prepared byemulsifying the reference product 8 was referred to as a pineapple-likeemulsified flavor composition of an invention product 34, one preparedby emulsifying the reference product 9 was referred to as that of aninvention product 35, one prepared by emulsifying the reference product10 was referred to as that of an invention product 36, one prepared byemulsifying the reference product 11 was referred to as that of aninvention product 37, one prepared by emulsifying the reference product12 was referred to as that of an invention product 38, and one preparedby emulsifying the reference product 13 was referred to as that of aninvention product 39.

Example 30: Addition of Pineapple-Like Compounded Flavor Composition toSherbet

According to the formulation of the following Table 13, sherbet wasprepared, and 0.2% of the pineapple-like emulsified flavor compositionof the invention products 34 to 39 was added thereto.

TABLE 13 Sugar 10 part by mass Starch syrup (75%) 6 ″ Fructose sucroseliquid sugar (75%) 5 ″ Citric acid (crystal) 0.1 ″ 20% pineapple juice10 ″ Water balance ″ Total 100 ″

Five panelists ate these sherbet products for organoleptic evaluation.As a result, all the five panelists concluded that the sherbet addedwith the invention products 34 to 39 had fresher and better pineapplecharacteristics of natural impression than the non-added sherbet, sayingthat, regarding the taste thereof, the former realized better umami andsweetness than the latter.

Example 101: Preparation of 2-(3-benzyloxypropyl)pyridine

An aqueous 25 wt % sodium hydroxide solution (44.24 g, 277 mmol),2-pyridinepropanol (5.00 g, 36.4 mmol), benzyl chloride (5.53 g, 43.7mmol) and tetra-n-butylammonium bromide (0.59 g, 1.8 mmol) were put intoa 200-mL flask, and stirred at 45° C. for 3 hours. The reaction liquidwas cooled down to room temperature, extracted with 50 mL of hexaneadded thereto, and the organic layer was separated. 2 Mol/l hydrochloricacid (50 mL) was added to the organic layer, and2-(3-benzyloxypropyl)pyridine was extracted out in the aqueous layer asa hydrochloride thereof. Subsequently, an aqueous 25 wt. % sodiumhydroxide solution was added to the aqueous layer to have a pH of 9 forneutralization of the hydrochloride, and then extracted with ethylacetate (50 mL). The organic layer was washed with 20% saline water (50mL), and dried with anhydrous magnesium sulfate added thereto. Thesolvent was evaporated away under reduced pressure using a rotaryevaporator to give a concentrated product (6.09 g). This was purifiedthrough distillation under reduced pressure to give2-(3-benzyloxypropyl)pyridine (yield: 4.34 g, 52.5%, purity: 99.6%)(invention product 101).

Physical Data of 2-(3-benzyloxypropyl)pyridine

Boiling point: 152 to 155° C./0.13 kPa

1H NMR (CDCl₃, 400 MHz) δ 2.07 (tt, 2H, J=7.8, 6.0 Hz), 2.89 (t, 2H,J=7.8 Hz), 3.53 (t, 2H, J=6.0 Hz), 4.51 (s, 2H), 7.10 (ddd, 1H, J=7.6,5.2, 1.2 Hz), 7.14 (d, 1H, J=7.6 Hz), 7.26-7.35 (m, 5H), 7.57 (dt, 1H,J=2.0, 7.6 Hz), 8.52 (dd, 1H, J=4.8, 0.8 Hz).

¹³C NMR (CDCl₃, 100 MHz) δ 29.65, 34.87, 69.56, 72.81, 120.95, 122.83,127.46, 127.59 (2C), 128.31 (2C), 136.22, 138.54, 149.24, 161.68.

MS (EI, 70 eV) m/z 65 (8), 78 (5), 91 (30), 92 (12), 93 (100), 94 (8),106 (13), 118 (6), 120 (15), 121 (10), 136 (86), 137 (8).

Example 102: Evaluation of Flavor of 2-(3-benzyloxypropyl)pyridine

A 0.1% ethanol solution of the invention product 101(2-(3-benzyloxypropyl)pyridine) prepared in Example 101 was prepared asan evaluation solution. The evaluation solution was prepared in a samplebottle. Regarding the flavor of the sample smelling from the bottlemouth and the flavor of a flavor paper prepared by infiltrating theevaluation solution into a paper, well-trained 5 panelists tested thesolution for flavor evaluation. A typical evaluation of the product isas follows.

Flavor evaluation (average evaluation of 5 panelists): somewhat herbal,green and nutty flavor of natural impression.

Example 103: Pineapple-Like Compounded Flavor Composition

According to the formulation of the following Table 14, a pineapple-likecompounded flavor composition was prepared to be a comparative product101.

TABLE 14 Ethyl acetate 12 part by mass Ethyl butyrate 10 ″ Isoamylacetate 4 ″ Isoamyl valerate 2.2 ″ Isobutyric acid 2.8 ″ Isovaleric acid1.2 ″ Allyl caproate 1.4 ″ Ethyl caproate 0.8 ″ Ethyl caprylate 0.6 ″Ethyl caprate 0.8 ″ Isoamyl alcohol 1.4 ″ Diethyl malonate 1.2 ″ Citral0.6 ″ Linalool 0.2 ″ Maltol 0.8 ″ Propylene glycol 500 ″ 95% ethanol 460″ Total 1000

0.2 g (0.02% by mass) of the invention product 101(2-(3-benzyloxypropyl)pyridine) was mixed in 999.8 g of theabove-mentioned, pineapple-like compounded flavor composition(comparative product 101) to prepare a novel pineapple-like compoundedflavor composition (invention product 102). Well-trained five panelistscompared the novel pineapple-like compounded flavor composition and theabove-mentioned pineapple compounded flavor composition not added withthe compound of the invention product 101. For flavor evaluation, 10 mlof the flavor composition was prepared in a sample bottle (30 ml). Thewell-trained five panelists evaluated the flavor smelling from thebottle mouth and the flavor of the flavor paper prepared by infiltratingthe flavor composition into a paper. As a result, all of the five expertpanelists concluded that the novel compounded flavor composition(invention product 102) added with the compound had fresher and betterpineapple characteristics of natural impression than the comparativeproduct 101 and was remarkably more excellent than the latter in pointof the flavor durability.

Example 104: Incorporation of Pineapple-Like Compounded FlavorComposition in Sherbet

The pineapple-like compounded flavor composition (comparative product101 or invention product 102) obtained in Example 103 was added tosherbet having the following formulation to prepare sherbet according toan ordinary method, and well-trained 5 panelists ate it for organolepticevaluation.

Sherbet Compounding Formulation (Part by Mass)

Sugar: 10, starch syrup (75%): 6, fructose sucrose liquid sugar syrup(75%): 5, citric acid (crystal): 0.1, 20% pineapple juice: 10, inventionproduct 102 (or comparative product 101): 0.2, water to make a totalamount of 100.

Five panelists ate these sherbet products for organoleptic evaluation.As a result, all the five panelists concluded that the sherbet addedwith the invention product 102 had fresher and better pineapplecharacteristics of natural impression than the sherbet added withcomparative product 101, and evaluated that, regarding the tastethereof, the former realized better umami and sweetness than the latter.

Example 105: Lilac-Type Compounded Flavor Composition

According to the formulation of the following Table 15, a lilac-typecompounded flavor composition was prepared (comparative product 102).

TABLE 15 Phenylethyl acetate 4 part by mass Cinnamic alcohol 16 ″Terpineol 52 ″ Cyclamen aldehyde 4 ″ Heliotropine 20 ″ Cinnamyl acetate4 ″ Carnation absolute 8 ″ Linalool 12 ″ Indole 0.8 ″ Styrax resinoid 12″ Ylang-ylang 4 ″ Hydroxycitronellal 116 ″ Benzyl acetate 8 ″Anisaldehyde 8 ″ Absolute jasmine 8 ″ Phenylethyl alcohol 111.2 ″ Anisealcohol 12 ″ 1,3-butylene glycol 600 ″ Total 1000

0.2 g (0.2% by mass) of 2-(3-benzyloxypropyl)pyridine was mixed in 99.8g of the above-mentioned lilac-type flavor composition (comparativeproduct 102) to prepare a novel lilac-type compounded flavor composition(invention product 103). Five panelists compared the novel compoundedflavor composition with the comparative product 102. As a result, allthe panelists concluded that the novel compounded flavor composition(invention product 103) added with the compound had fresher lilaccharacteristics of natural impression than the comparative product 102and was remarkably more excellent than the latter in point of the flavordurability.

Example 106: Incorporation of Lilac-Type Compounded Flavor Compositionin Shampoo

The lilac-type compounded flavor composition (comparative product 102 orinvention product 103) obtained in Example 105 was added to shampoohaving the following formulation to prepare shampoo according to anordinary method, and well-trained 5 panelists tried it in shampooing fororganoleptic evaluation.

Shampoo Formulation (Part by Mass)

Sodium polyoxyethylene laurylsulfate: 20, coconut oil fatty aciddiethanolamide: 5, glycerin: 4, invention product 103 (or comparativeproduct 102); 0.2, water to make a total amount of 100.

Five panelists tested these shampoo products for organolepticevaluation. As a result, all the five panelists concluded that theshampoo added with the invention product 103 had fresher and betterlilac characteristics of natural impression than the shampoo added withthe comparative product 102.

Example 107: Confirmation of Umami

A solution was prepared by dissolving 2-(3-benzyloxypropyl)pyridine(invention product 101) in water to have a concentration shown in Table15. As a comparative product, a solution was prepared by dissolving2-(2-benzyloxyethyl)pyridine (comparative product 1 prepared inComparative Example 1) to have the same concentration. Well-trained 5panelists tasted the solutions and non-added water for organolepticevaluation of taste and flavor.

Average evaluation results of the five panelists are shown in thefollowing Table 16.

TABLE 16 Organoleptic Evaluation 2-(3-benzyloxypropyl)pyridine2-(2-benzyloxyethyl)pyridine Addition (invention product 101)(comparative product 1) Concentration Taste Flavor Taste Flavor   2 ppbNo difference from Nothing at all. No difference from Nothing at all.water. water.  10 ppb Slightly umami Extremely slightly No differencefrom Nothing at all. somewhat herbal, green water. and nutty flavor ofnatural impression.   0.1 ppm Weakly umami. Slightly somewhat Slightlyumami. Extremely slightly herbal, green and nutty earthy flavor flavorof natural associated with fresh impression. grass roots.   1 ppm Umami.The quality of Somewhat herbal, green Weakly umami. Slightly earthyflavor umami is natural and and nutty flavor of associated with freshappetizing. natural impression. grass roots.  20 ppm Strongly umami.Somewhat herbal, green Umami. The quality of Earthy flavor and nuttyflavor of umami is natural and associated with fresh natural impression.appetizing. grass roots.  200 ppm Extremely strong Somewhat herbal,green Strongly umami. Earthy flavor umami, but associated and nuttyflavor of associated with fresh with bitterness. natural impression.grass roots.  500 ppm Strong umami and Too strong flavor and Extremelystrong Extremely strong bitterness, and the poor balance. umami, butassociated earthy flavor balance of the two is with bitterness.associated with fresh not good. grass roots. 2000 ppm Strong umami andToo strong flavor and Strong umami and Too strong flavor and bitterness,and the poor balance. bitterness, and the poor balance. balance of thetwo is balance of the two is not good. not good.

As shown in Table 16, the aqueous solution prepared by dissolving2-(3-benzyloxypropyl)pyridine (invention product 101) alone in water wastasty, and the taste thereof was umami. Regarding the concentration, itis known that the compound gave umami in an amount falling within arange of, by mass, 0.01 ppm to 200 ppm, and gave especially good umamiwithin a range of 0.1 ppm to 20 ppm or so.

On the other hand, the aqueous solution prepared by dissolving2-(2-benzyloxyethyl)pyridine (comparative product 1) alone in water wasalso tasty and the taste thereof was umami. It is known that thesolution provided umami when the concentration fell within a range of0.1 ppm to 2000 ppm by mass, and in particular, provided good umami whenthe concentration was 1 ppm to 200 ppm or so.

Specifically, it is recognized that the umami imparting effect of2-(3-benzyloxypropyl)pyridine is stronger by 10 times or so than2-(2-benzyloxyethyl)pyridine, and the concentration of2-(3-benzyloxypropyl)pyridine to provide the same umami intensity wasabout 1/10 that of 2-(2-benzyloxyethyl)pyridine.

Example 108: Confirmation of Umami Imparting and Saltiness EnhancingEffect

An aqueous 0.3 mass % sodium chloride solution (control), and solutionsof 2-(3-benzyloxypropyl)pyridine dissolved in a 0.3 mass % sodiumchloride solution to have the concentration shown in Table 17 wereprepared. As comparative products, an aqueous 0.3 mass % sodium chloridesolution (control), and a solution of a comparative product,2-(2-benzyloxyethyl)pyridine dissolved in a 0.3 mass % sodium chloridesolution to have the same concentration were prepared. Well-trained 5panelists tasted the solutions for organoleptic evaluation of umamiimpartment and saltiness enhancement. Average evaluation results areshown in the following Table 17.

TABLE 17 Organoleptic Evaluation Addition 2-(3-benzyloxypropyl)pyridine(invention 2-(2-benzyloxyethyl)pyridine (comparative Concentrationproduct 101) product 1) 0.05 ppb No difference from control (aqueous 0.3No difference from control (aqueous 0.3 mass % mass % sodium chloridesolution). sodium chloride solution).  0.1 ppb Extremely slightly umamiand saltiness, as No difference from control (aqueous 0.4 mass %compared with control. sodium chloride solution).   1 ppb Slightly umamias compared with control. Extremely slightly umami as compared withcontrol.   10 ppb Umami and saltiness as compared with Slightly umami ascompared with control. control.  0.1 ppm Distinctly umami and saltinessas compared Umami as compared with control. with control. The quality ofumami and saltiness is good, natural and appetizing.  0.5 ppm Stronglyumami and saltiness as compared Distinctly umami as compared withcontrol. with control. The quality of umami and The quality of umami isgood, natural and saltiness is good, natural and appetizing. appetizing.  2 ppm Extremely strongly umami and saltiness as Strongly umami ascompared with control. The compared with control, but somewhat tooquality of umami is good, natural and much. appetizing.   10 ppm Toomuch umami and saltiness as compared Extremely strongly umami ascompared with with control, additionally somewhat control, but somewhattoo much. bitterness.   50 ppm Too much umami and saltiness as comparedToo much umami as compared with control, with control, additionallysomewhat additionally somewhat bitterness. bitterness.

As shown in Table 17, the aqueous solution prepared by dissolving2-(3-benzyloxypropyl)pyridine (invention product 101) in an aqueous 0.3mass % sodium chloride solution had umami and salty taste, and thesolution provided umami at a lower concentration by about 1/10 than thatof the solution prepared by dissolving the product in water.Accordingly, the concentration of 2-(3-benzyloxypropyl)pyridine capableof realizing umami impartation and saltiness enhancement when combinedwith edible salt is considered to be within a range of 1 ppb to 200 ppmby mass, preferably 0.01 ppm to 50 ppm, more preferably 0.1 ppm to 10ppm. In addition, it is recognized that the umami imparting effect of2-(3-benzyloxypropyl)pyridine is higher by about 10 times than that of2-(2-benzyloxyethyl)pyridine (comparative product 1), and theconcentration of 2-(3-benzyloxypropyl)pyridine to realize the samedegree of umami intensity is about 1/10 that of2-(2-benzyloxyethyl)pyridine.

Example 109: Confirmation of Umami and Saltiness Enhancement

Well-trained 5 panelists tasted an aqueous solution of 0.3 mass % ediblesalt and 0.03 mass % sodium glutamate (MSG), and an aqueous solutionprepared by adding to the aqueous solution, 10 ppb of2-(3-benzyloxypropyl)pyridine (invention product 101), for organolepticevaluation in point of umami and saltiness enhancement. As a result, allthe five panelists concluded that the aqueous solution added with 10 ppbof 2-(3-benzyloxypropyl)pyridine gave stronger umami and saltiness.

Example 110: Confirmation of Umami Enhancing Effect

Well-trained 5 panelists tasted an aqueous solution of 0.3 mass % ediblesalt and 0.05 mass % sodium glutamate (MSG), and an aqueous solution of0.3 mass % edible salt and 10 ppb of 2-(3-benzyloxypropyl)pyridine(invention product 101), for organoleptic evaluation of umami. As aresult, all the five panelists concluded that the two had umami ofalmost the same level.

Example 111: Confirmation of Umami Enhancing Effect

Well-trained 5 panelists tasted an aqueous solution of 0.1 mass % sodiuminosinate (5′-IMP.2Na), and an aqueous solution prepared by addingthereto 10 ppb of 2-(3-benzyloxypropyl)pyridine (invention product 101),for organoleptic evaluation in point of umami. As a result, all the fivepanelists concluded that the aqueous solution added with 10 ppb of2-(3-benzyloxypropyl)pyridine gave stronger umami.

Example 112: Confirmation of Sweetness Enhancing Effect

Well-trained 5 panelists tasted an aqueous 3 mass % sucrose solution,and an aqueous solution prepared by adding thereto 5 ppb of2-(3-benzyloxypropyl)pyridine (invention product 101), for organolepticevaluation in point of sweetness. As a result, all the five panelistsconcluded that the aqueous solution added with 5 ppb of2-(3-benzyloxypropyl) pyridine gave stronger sweetness.

Example 113: Addition to Soup Broth for Udon Noodle

0.05 ppm of 2-(3-benzyloxypropyl)pyridine (invention product 101) wasadded to commercially-available soup broth for udon noodle (tripestrength). 200 ml of hot water was added to 100 ml of each of the addedsoup broth and the non-added soup broth, and well-trained 5 paneliststasted them for organoleptic evaluation in point of umami. As a result,all the five panelists concluded that the soup broth added with 0.05 ppmof 2-(3-benzyloxypropyl)pyridine provided stronger umami, saltiness andsweetness.

Example 114: Katsuobushi-Like Compounded Flavor Composition (a Type thatImparts Umami in Addition to Flavor)

According to the formulation of the following Table 18, akatsuobushi-like compounded flavor composition was prepared.

TABLE 18 1,2,3-trimethoxy-5-methylbenzene 40 part by mass Isosafrole 2 ″2-penten-1-ol 8 ″ Trans-2-pentenal 1 ″ Cyclotene 10 ″ Diacetyl 5 ″2-methylfuran 20 ″ Acetic acid 3 ″ γ-butyrolactone 1 ″(E,Z,Z)-2,4,7-tridecatrienal 0.00005 ″ 4,7-tridecadienal 0.00005 ″Trimethylamine 0.00001 ″ 2-methylfuran-3-thiol 0.00005 ″2-(3-benzyloxypropyl)pyridine 1 ″ 95% ethanol 100 ″ Propylene glycolbalance ″ Total 1000

Example 115: Addition of Katsuobushi-Like Compounded Flavor Compositionto Mentsuyu

According to the formulation of the following Table 19, mentsuyu wasprepared, and 0.02% of the katsuobushi-like compounded flavorcomposition prepared in Example 114 was added thereto.

TABLE 19 Soy sauce 500 Part by mass Mirin 200 ″ Sugar 100 ″ Yeastextract 6 ″ Water 194 ″ Total 1000

Well-trained 5 panelists tasted the mentsuyu not added with thekatsuobushi-like compounded flavor composition and the katsuobushi-likecompounded flavor composition-added mentsuyu for organolepticevaluation. As a result, all the five panelists concluded that thementsuyu added with the katsuobushi-like compounded flavor compositionof the present invention was good as given a katsuobushi-like flavor,additionally saying that the taste thereof covered enhanced umami,saltiness and sweetness, that is, the mentsuyu was extremely deliciousand good.

Example 116: Milk-Like Compounded Flavor Composition (a Type thatImparts Richness in Addition to Flavor)

According to the formulation of the following Table 20, a milk-likecompounded flavor composition (comparative product 104) was prepared.

TABLE 20 Vanillin 25.0 part by mass Ethylvanillin 35.0 ″ Maple lactone2.5 ″ Ethylmaltol 3.5 ″ γ-undecalactone 2.0 ″ γ-nonalactone 10.0 ″δ-decalactone 2.5 ″ Acetylmethylcarbinol 3.0 ″ Diacetyl 7.0 ″ Butyricacid 5.0 ″ Propylene glycol 904.5 ″ Total 1000.0 ″

One mg (10 ppm) of 2-(3-benzyloxypropyl)pyridine was mixed in 100 g ofthe milk-like compounded flavor composition (comparative product 104) toprepare a milk-like compounded flavor composition of an inventionproduct 104.

Example 117: Addition to Aqueous Solution of Skim Milk

A mixed solution (aqueous solution of skin milk) of 10 parts by mass ofskim milk and 90 parts by mass of water was prepared, and 0.1% of themilk-like compounded flavor composition prepared in Example 116 wasadded thereto. Well-trained 5 panelists tasted the aqueous solution ofskim milk not added with the milk-like compounded flavor composition,the aqueous solution of skim milk added with 0.1% by mass of any of thecomparative product 104 and the aqueous solution of skim milk added with0.1% by mass of any of the invention product 104 for organolepticevaluation. As a result, all the five panelists concluded that theaqueous solution of skim milk added with the comparative product 104 wasbetter-tasting than the non-added aqueous solution of skim milk as givenenriched milk flavor, further saying that the aqueous solution of skimmilk added with the invention product 104 was extremely better than theaqueous solution of skim milk added with the comparative product 104 asgiven stronger umami and sweetness and further given stronger milkrichness, that is, the former had an extremely good milk-like taste.

Reference Example 201: Confirmation of Umami

The invention product 101 and the comparative product 1 wereindividually diluted with ethanol to have a proper concentration, andthen further diluted with water to prepare an aqueous solution of2-(3-benzyloxypropyl)pyridine (invention product 101 produced in Example101) and that of 2-(2-benzyloxyethyl)pyridine (comparative product 1synthesized in Comparative Example 1) each having a concentration shownin the following Table 21. Well-trained panelists tasted the solutionhaving a different concentration and non-added water for organolepticevaluation in point of taste and flavor.

Average evaluation results of the five panelists are shown in Table 21.

TABLE 21 Organoleptic Evaluation 2-(3-benzyloxypropyl)pyridine2-(2-benzyloxyethyl)pyridine Addition (invention product 101)(comparative product 1) Concentration Taste Flavor Taste Flavor  2 ppbNo difference from Nothing at all. No difference from Nothing at all.water. water.  10 ppb Slightly umami. Extremely slightly No differencefrom Nothing at all. somewhat herbal, green water. and nutty flavor ofnatural impression.  0.1 ppm Weakly umami. Slightly somewhat Slightlyumami. Extremely slightly herbal, green and nutty earthy flavor flavorof natural associated with fresh impression. grass roots.  1 ppm Umami.The quality of Somewhat herbal, green Weakly umami. Slightly earthyflavor umami is natural and and nutty flavor of associated with freshappetizing. natural impression. grass roots.  20 ppm Strongly umami.Somewhat herbal, green Umami. The quality of Earthy flavor and nuttyflavor of umami is natural and associated with fresh natural impression.appetizing. grass roots. 200 ppm Extremely strong Somewhat herbal, greenStrongly umami. Earthy flavor umami, but associated and nutty flavor ofassociated with fresh with bitterness. natural impression. grass roots.

As shown in Table 21, the aqueous solution of2-(3-benzyloxypropyl)pyridine (invention product 101) was tasty, and thetaste thereof was umami. Regarding the concentration, it is known thatthe compound gave umami in an amount falling within a range of, by mass,0.01 ppm to 200 ppm, and gave especially good umami within a range of0.1 ppm to 20 ppm or so.

On the other hand, the aqueous solution of 2-(2-benzyloxyethyl)pyridine(comparative product 1) was also tasty and the taste thereof was umami.It is known that the solution provided umami when the concentration fellwithin a range of 0.1 ppm to 2000 ppm by mass, and in particular,provided good umami when the concentration was 1 ppm to 200 ppm or so.

Specifically, it is recognized that the umami imparting effect of2-(3-benzyloxypropyl)pyridine is stronger by 10 times or so than2-(2-benzyloxyethyl)pyridine, and the concentration of2-(3-benzyloxypropyl)pyridine to provide the same umami intensity wasabout 1/10 that of 2-(2-benzyloxyethyl)pyridine.

Example 201: Preparation of Emulsified Composition Containing2-(3-benzyloxypropyl)pyridine

As an oily phase, 2-(3-benzyloxypropyl)pyridine (1.0 g), SAIB (sucroseacetate isobutyrate) (9.0 g) and MCT (middle-chain fatty acidtriglyceride) (9.0 g) were mixed and dissolved, and as an aqueous phase,66 g of glycerin, 11 g of ion-exchanged water and decaglycerinmonooleate (4.0 g) were mixed and dissolved, and the two liquids weremixed by stirring with a TK-homogenizer (manufactured by PrimixCorporation) at 8000 rpm for 10 minutes for emulsification. Thus, an O/Wemulsion was prepared, whose absorbance at a wavelength 680 nm in 1/2000dilution with ion-exchanged water was 0.2 Abs (invention product 201:2-(3-benzyloxypropyl)pyridine concentration 1.0%).

Reference Example 202: Ethanol Solution of 2-(3-benzyloxypropyl)pyridine

2-(3-Benzyloxypropyl)pyridine (1.0 g) was dissolved in 99.0 g of 99.5%ethanol to prepare a solution thereof (reference product 202:2-(3-benzyloxypropyl)pyridine concentration 1.0%).

Example 202: Confirmation of Umami

The invention product 201 and the reference product 202 was individuallydissolved in water to prepare a 2-(3-benzyloxypropyl)pyridine solutionhaving a concentration shown in the following Table 22. Well-trained 5panelists tasted the solutions for organoleptic evaluation in point oftaste and flavor

Average evaluation results of the five panelists are shown in Table 22.

TABLE 22 Organoleptic Evaluation 2-(3-Benzyl- Emulsified ProductEthanol-Diluted Product oxypropyl)pyridine (invention product 201)(reference product 202) Concentration Taste Flavor Taste Flavor  2 ppbNo difference from water. Nothing at all. No difference from Nothing atall. water.  10 ppb Slightly umami. As compared Extremely slightlySlightly umami. Extremely slightly with ethanol-diluted somewhat herbal,green somewhat herbal, product, mild but and nutty flavor of green andnutty flavor persistent. natural impression. of natural impression.  0.1ppm Weakly umami. As compared Slightly somewhat Weakly umami. Slightlysomewhat with ethanol-diluted herbal, green and nutty herbal, green andproduct, mild but flavor of natural nutty flavor of persistent.impression. natural impression.  1 ppm Umami. The quality of umamiSomewhat herbal, green Umami. The quality of Somewhat herbal, is naturaland appetizing. and nutty flavor of umami is natural and green and nuttyflavor As compared with natural impression. appetizing. of naturalethanol-diluted product, impression. mild but persistent.  20 ppmStrongly umami. As compared Somewhat herbal, green Strongly umami.Somewhat herbal, with ethanol-diluted and nutty flavor of green andnutty flavor product, mild but natural impression. of naturalpersistent. impression. 200 ppm Extremely strong umami, but Somewhatherbal, green Strongly umami. Earthy flavor associated with bitterness.and nutty flavor of associated with fresh As compared with naturalimpression. green roots. ethanol-diluted product, mild but persistent.

As shown in Table 22, both the aqueous dilution of the ethanol-diluted2-(3-benzyloxypropyl)pyridine (reference product 202) and the aqueousdilution of the emulsified product (invention product 201) had umami,but the result was that the emulsified product was milder and morepersistent than the ethanol-diluted product having the same2-(3-benzyloxypropyl)pyridine concentration.

Example 203: Confirmation of Umami Imparting and Saltiness EnhancingEffect

An aqueous 0.3 mass % sodium chloride solution (control), and solutionsof the invention product 201 or the reference product 202 dissolved in a0.3 mass % sodium chloride solution to have the concentration as2-(3-benzyloxypropyl)pyridine therein shown in the following Table 23were prepared. Well-trained 5 panelists tasted the solutions fororganoleptic evaluation of umami impartment and saltiness enhancement.Average evaluation results are shown in Table 23.

TABLE 23 2-(3-Benzyl- oxypropyl)pyridine Addition OrganolepticEvaluation Concentration Emulsified Product (invention product 201)Ethanol Dilution (reference product 202) 0.05 ppb No difference fromcontrol (aqueous 0.3 mass % No difference from control (aqueous 0.3 mass% sodium chloride solution). sodium chloride solution).  0.1 ppbExtremely slightly umami and saltiness, as Extremely slightly umami andsaltiness, as compared with control. compared with control.   1 ppbSlightly umami as compared with control. Slightly umami as compared withcontrol.   10 ppb Umami and saltiness as compared with control. Umamiand saltiness as compared with control. Milder and more persistent thanethanol dilution.  0.1 ppm Distinctly umami and saltiness as comparedDistinctly umami and saltiness as compared with control. The quality ofumami and with control. The quality of umami and saltiness is good,natural and appetizing. saltiness is good, natural and appetizing.Milder and more persistent than ethanol dilution having the sameconcentration  0.5 ppm Strongly umami and saltiness as compared withStrongly umami and saltiness as compared with control. The quality ofumami and saltiness control. The quality of umami and saltiness is good,natural and appetizing. Milder and is good, natural and appetizing. morepersistent than ethanol dilution having the same concentration  2 ppmExtremely strongly umami and saltiness as Extremely strongly umami andsaltiness as compared with control. Natural umami and compared withcontrol, but somewhat too much. saltiness without too much taste likeethanol dilution.  10 ppm Too much umami and saltiness as compared withToo much umami and saltiness as compared with control, additionallystrong bitterness. control, additionally somewhat bitterness. Not toomuch like ethanol dilution having the same concentration.  50 ppm Toomuch umami and saltiness as compared with Too much umami and saltinessas compared with control, additionally strong bitterness. control,additionally somewhat bitterness. Not too much like ethanol dilutionhaving the same concentration.

As shown in Table 23, the aqueous solution prepared by dissolving2-(3-benzyloxypropyl)pyridine in an aqueous 0.3 mass % sodium chloridesolution had umami and salty taste, and the solution provided umami at alower concentration by about 1/10 than that of the solution prepared bydissolving the product in water. Accordingly, the concentration of2-(3-benzyloxypropyl)pyridine capable of realizing umami impartation andsaltiness enhancement when combined with edible salt is considered to bewithin a range of 0.1 ppb to 50 ppm by mass, preferably 1 ppb to 10 ppm,more preferably 10 ppb to 2 ppm.

In addition, the emulsified product of 2-(3-benzyloxypropyl)pyridinegave milder and more persistent umami and saltiness than the ethanoldilution thereof. In particular, it is recognized that, when having ahigh concentration (0.5 ppm or more), too much umami of the emulsifiedproduct is reduced more as compared with the ethanol dilution, and theemulsified product realized milder and persistent umami.

Example 204: Confirmation of Umami and Saltiness Enhancement

Well-trained 5 panelists tasted an aqueous solution of 0.3 mass % ediblesalt and 0.03 mass % sodium glutamate (MSG), and an aqueous solutionprepared by adding to the aqueous solution, 10 ppb, as2-(3-benzyloxypropyl)pyridine therein, of the invention product 201 orthe reference product 202, for organoleptic evaluation in point of umamiand saltiness enhancement. As a result, all the five panelists concludedthat the aqueous solution added with 10 ppb of2-(3-benzyloxypropyl)pyridine gave stronger umami and saltiness, andthat the aqueous solution added with the invention product 201(emulsified product) had milder and more persistent umami and saltinessthan that added with the reference product 202 (ethanol dilution).

Example 205: Confirmation of Umami Enhancing Effect

Well-trained 5 panelists tasted (1) an aqueous solution of 0.3 mass %edible salt and 0.05 mass % sodium glutamate (MSG), and (2) and anaqueous solution of 0.3 mass % edible salt and 10 ppb, as2-(3-benzyloxypropyl)pyridine therein, of the invention product 201, fororganoleptic evaluation in point of umami. As a result, all the fivepanelists concluded that both the two [(1) and (2)] had nearly the samelevel of umami.

Example 206: Confirmation of Umami Enhancing Effect

Well-trained 5 panelists tasted (1) 0.1 mass % sodium inosinate(5′-IMP.2Na) and (2) an aqueous solution of 0.1 mass % sodium inosinateand 5 ppb, as 2-(3-benzyloxypropyl)pyridine therein, of the inventionproduct 201, for organoleptic evaluation in point of umami. As a result,all the five panelists concluded that (2) added with 5 ppb of2-(3-benzyloxypropyl)pyridine had stronger umami.

Example 207: Confirmation of Sweetness Enhancing Effect

Well-trained 5 panelists tasted (1) an aqueous 3 mass % sucrose solutionand (2) an aqueous solution prepared by adding 5 ppb, as2-(3-benzyloxypropyl)pyridine therein, of the invention product 201 tothe aqueous 3 mass % sucrose solution, for organoleptic evaluation inpoint of sweetness. As a result, all the five panelists concluded that(2) added with 5 ppb of 2-(3-benzyloxypropyl)pyridine had strongersweetness.

Example 208: Addition to Soup Broth for Udon Noodle

0.05 ppm as 2-(3-benzyloxypropyl)pyridine therein of the inventionproduct 201 was added to commercially-available soup broth for udonnoodle (tripe strength). 200 ml of hot water was added to 100 ml of eachof the added soup broth and the non-added soup broth, and well-trained 5panelists tasted them for organoleptic evaluation in point of umami. Asa result, all the five panelists concluded that the soup broth addedwith 0.05 ppm of 2-(3-benzyloxypropyl)pyridine provided stronger umami,saltiness and sweetness.

Example 209: Katsuobushi-Like Emulsified Flavor Composition

According to the formulation of the following Table 24, akatsuobushi-like compounded flavor composition (reference product 203)was prepared.

TABLE 24 1,2,3-trimethoxy-5-methylbenzene 40 part by mass Isosafrole 2 ″2-penten-1-ol 8 ″ Trans-2-pentenal 1 ″ Cyclotene 10 ″ Diacetyl 5 ″2-methylfuran 20 ″ Acetic acid 3 ″ γ-butyrolactone 1 ″(E,Z,Z)-2,4,7-tridecatrienal 0.00005 ″ 4,7-tridecadienal 0.00005 ″Trimethylamine 0.00001 ″ 2-methylfuran-3-thiol 0.00005 ″2-(3-benzyloxypropyl)pyridine 1 ″ Middle chain fatty acid triglyceridebalance ″ Total 100

100 g of the katsuobushi-like compounded flavor composition of the aboveTable 24 (referenced product 203: 2-(3-benzyloxypropyl)pyridineconcentration 1.0 mass %) as an oily phase, and a solution of 312.5 g ofglycerin, and 22.5 g of decaglycerin monostearate dissolved in 65 g ofion-exchanged water as an aqueous phase were prepared. The two weremixed by stirring with a TK-homogenizer (manufactured by PrimixCorporation) at 8000 rpm for 10 minutes for emulsification. Thus, akatsuobushi-like emulsified flavor composition in the form of an O/Wemulsion was prepared, whose absorbance at a wavelength 680 nm in 1/2000dilution with ion-exchanged water was 0.2 Abs (invention product 202:2-(3-benzyloxypropyl)pyridine concentration 0.2% by mass).

Example 210: Addition of Katsuobushi-Like Emulsified Flavor Compositionto Mentsuyu

According to the formulation of the following Table 25, mentsuyu wasprepared, and 0.01% of the katsuobushi-like emulsified flavorcomposition of the invention product 202 was added thereto(2-(3-benzyloxypropyl)pyridine concentration 0.2 ppm).

TABLE 25 Soy sauce 500 Part by mass Mirin 200 ″ Sugar 100 ″ Yeastextract 6 ″ Water 194 ″ Total 1000

Well-trained 5 panelists tasted the mentsuyu not added with thekatsuobushi-like emulsified flavor composition and the katsuobushi-likecompounded flavor composition-added mentsuyu for organolepticevaluation. As a result, all the five panelists concluded that thementsuyu added with the katsuobushi-like emulsified flavor compositionof the present invention was good as given a katsuobushi-like flavor,additionally saying that the taste thereof covered enhanced umami,saltiness and sweetness, that is, the mentsuyu was extremely deliciousand good.

Example 211: Katsuobushi-Like Powdery Flavor Composition

As an aqueous phase, 70 g of gum arabic and 20 g of trehalose weredissolved in 150 g of water, and sterilized by heating at 85 to 90° C.for 15 minutes, and then cooled down to 40° C. As an oily phase, 10 g ofthe reference product 203 was added thereto and mixed, and thenemulsified with a TK-homogenizer to produce an O/W emulsifiedcomposition. The emulsified composition was spray-dried, using a mobileminor spray drier by Niro, at an inlet temperature of 140° C. and anoutlet temperature of 75° C. to produce 95 g of a katsuobushi-likepowdery flavor composition (invention product 203:2-(3-benzyloxypropyl)pyridine concentration 0.1% by mass).

Example 212: Addition of Katsuobushi-Like Powdery Flavor Composition toPowdery Ramen Soup

Powdery ramen soup was prepared according to the formulation of Table26. 1% by mass of the invention product 203 was further added thereto.

TABLE 26 Amount Added (part by mass) Edible salt 360 Powdered soy sauce220 Sodium L-glutamate 120 Meat extract powder 100 Sugar 80 Seafoodextract powder 30 Vegetable extract powder 20 Spice powder 10 Sodiumsuccinate 5 Dextrin 55 Total 1000

Powdery ramen soup added with the invention product 203 and that notadded with it were prepared each in an amount of 10 g, 600 ml/one of hotwater (70° C.) was added to dilute them, and well-trained 5 paneliststasted them for organoleptic evaluation. As a result, all the fivepanelists concluded that the ramen soup added with the katsuobushi-likepowdery flavor composition of the invention was better as given akatsuobushi-like flavor, additionally saying that the composition-addedramen soup was an extremely better-tasting one as given greatly enhancedumami, saltiness and sweetness.

Example 213: Milk-Like Emulsified Flavor Composition

According to the formulation of the following Table 27, milk-likecompounded flavor compositions (reference product 204 and referenceproduct 205) were prepared.

TABLE 2 Milk-like Compounded Flavor Formulation Reference ReferenceProduct 204 Product 205 Vanillin 25.0 25.0 part by mass Ethylvanillin35.0 35.0 ″ Maple lactone 2.5 2.5 ″ Ethylmaltol 3.5 3.5 ″γ-undecalactone 2.0 2.0 ″ γ-nonalactone 10.0 10.0 ″ δ-decalactone 2.52.5 ″ Acetylmethylcarbinol 3.0 3.0 ″ Diacetyl 7.0 7.0 ″ Butyric acid 5.05.0 ″ 2- 10.0 — ″ (3-benzyloxypropyl)pyridine Middle chain fatty acidbalance balance ″ triglyceride Total 1000.0 1000.0 ″

100 g of the milk-like compounded flavor composition of Table 27(referenced product 204: 2-(3-benzyloxypropyl)pyridine concentration 1.0mass %, or reference product 205: not using2-(3-benzyloxypropyl)pyridine) as an oily phase, and a solution of 312.5g of glycerin, and 22.5 g of decaglycerinmonopalmitake dissolved in 65 gof ion-exchanged water as an aqueous phase were prepared. The two weremixed by stirring with a TK-homogenizer (manufactured by PrimixCorporation) at 8000 rpm for 10 minutes for emulsification. Thus, amilk-like emulsified flavor composition in the form of an O/W emulsionwas prepared, whose absorbance at a wavelength 680 nm in 1/2000 dilutionwith ion-exchanged water was 0.2 Abs (invention product 204:2-(3-benzyloxypropyl)pyridine concentration 0.2% by mass, comparativeproduct 202: not using 2-(3-benzyloxypropyl)pyridine).

Example 214: Addition of Milk-Like Emulsified Flavor Composition toLacto-Ice

According to the formulation of the following Table 28, lacto-ice wasprepared, and 0.01% of the milk-like compounded flavor composition ofthe invention product 204 or the comparative product 202 was addedthereto (2-(3-benzyloxypropyl)pyridine concentration in the lacto-iceusing the invention product 204, 0.2 ppm). For preparing lacto-ice, allthe materials were dissolved by heating and emulsified with ahomogenizer at 150 kg/cm², and then aged overnight at 10° C. This wasfrozen with a freezer, and then hardened up at −40° C. for 1 hour togive lacto-ice.

TABLE 28 Sweetened condensed milk 4 part by mass Skim milk 7 ″ Vegetableoil and fat 9 ″ Sugar 10 ″ Egg yolk 12.5 ″ Stabilizer 0.3 ″ Emulsifier0.4 ″ Vanilla flavor 0.1 ″ water balance ″ Total 100 ″

Well-trained 5 panelists tasted the lacto-ice added with the milk-likeemulsified flavor composition of the comparative product 202 or theinvention product 204, and the non-added lacto-ice for organolepticevaluation. As a result, all the five panelists first concluded that thelacto-ice added with the comparative product 202 provided bettermilk-like flavor than the lacto-ice not added with the flavor. Further,all the five panelists concluded that the lacto-ice added with theinvention product 204 provided better milk-like flavor than thelacto-ice added with the comparative product 202 and that, regardingtaste, the former provided enhanced umami, sweetness and milk richnessand was extremely delicious and good.

Example 215: Milk-Like Powdery Flavor Composition

As an aqueous phase, 70 g of gum arabic and 20 g of trehalose weredissolved in 150 g of water, and sterilized by heating at 85 to 90° C.for 15 minutes, and then cooled down to 40° C. As an oily phase, 10 g ofthe reference product 204 was added thereto and mixed, and thenemulsified with a TK-homogenizer to produce an O/W emulsifiedcomposition. The emulsified composition was spray-dried, using a mobileminor spray drier by Niro, at an inlet temperature of 140° C. and anoutlet temperature of 75° C. to produce 95 g of a milk-like powderyflavor composition (invention product 205: 2-(3-benzyloxypropyl)pyridineconcentration 0.1% by mass).

Example 216: Addition to Aqueous Solution of Skim Milk

Skim milk, and a mixture of 99 parts by mass of skim milk and 1 part bymass of the invention product 205 were prepared by thorough mixing. 10parts by mass of each was mixed with 90 parts by mass of water toprepare a mixture solution (aqueous solution of skim milk). Well-trained5 panelists tasted these for organoleptic evaluation. As a result, allthe five panelists concluded that the aqueous solution of skim milkadded with the invention product 205 was better than the non-addedaqueous solution of skim milk in that the former provided stronger milkyflavor, stronger umami and sweetness, and stronger milk richness,namely, the former had an extremely good milky taste.

Example 217: Pineapple-Like Emulsified Flavor Composition

According to the formulation of the following Table 29, a pineapple-likecompounded flavor composition was prepared (reference product 206).

TABLE 29 Ethyl acetate 12 part by mass Ethyl butyrate 10 ″ Isoamylacetate 4 ″ Isoamyl valerate 2.2 ″ Isobutyric acid 2.8 ″ Isovaleric acid1.2 ″ Allyl caproate 1.4 ″ Ethyl caproate 0.8 ″ Ethyl caprylate 0.6 ″Ethyl caprate 0.8 ″ Isoamyl alcohol 1.4 ″ Diethyl malonate 1.2 ″ Citral0.6 ″ Linalool 0.2 ″ Maltol 0.8 ″ 2-(3-benzyloxypropyl)pyridine 0.2 ″Middle-chain fatty acid triglyceride balance ″ Total 1000

As an oily phase, 100 g of the pineapple-like compounded flavorcomposition of Table 29 (reference product 206:2-(3-(benzyloxypropyl)pyridine concentration 0.02% by mass), and as anaqueous phase, 312.5 g of glycerin and 22.5 g of decaglycerin monooleatedissolved in 65 g of ion-exchanged water were prepared, and the twoliquids were mixed by stirring with a TK-homogenizer (manufactured byPrimix Corporation) at 8000 rpm for 10 minutes for emulsification. Thus,a pineapple-like emulsified flavor composition in the form of an O/Wemulsion was prepared, whose absorbance at a wavelength 680 nm in 1/2000dilution with ion-exchanged water was 0.2 Abs (invention product 206:2-(3-benzyloxypropyl)pyridine concentration 40 ppm).

Example 218: Addition of Pineapple-Like Compounded Flavor Composition toSherbet

According to the formulation of the following Table 30, sherbet wasprepared, and 0.2% of the pineapple-like emulsified flavor compositionof the invention product 206 was added thereto(2-(3-benzyloxypropyl)pyridine concentration 80 ppb).

Five panelists ate these sherbet products for organoleptic evaluation.As a result, all the five panelists concluded that the sherbet addedwith the invention product 206 had fresher and better pineapplecharacteristics of natural impression than the non-added sherbet, sayingthat, regarding the taste thereof, the former realized better umami andsweetness than the latter.

TABLE 30 Sugar 10 part by mass Starch syrup (75%) 6 ″ Fructose sucroseliquid sugar (75%) 5 ″ Citric acid (crystal) 0.1 ″ 20% pineapple juice10 ″ Water balance ″ Total 100 ″

While the present invention has been described in detail and withreference to specific embodiments thereof, it will be apparent to oneskilled in the art that various changes and modifications can be madetherein without departing from the spirit and scope thereof.

The present disclosure relates to the subject matter contained inInternational Application No. PCT/JP2016/061077, filed Apr. 5, 2016,Japanese Patent Application No. 2015-083656 filed on Apr. 15, 2015,Japanese Patent Application No. 2015-181420 filed on Sep. 15, 2015 andJapanese Patent Application No. 2015-206337 filed on Oct. 20, 2015, thecontents of which are expressly incorporated herein by reference intheir entirety. All the publications referred to in the presentspecification are also expressly incorporated herein by reference intheir entirety.

The foregoing description of preferred embodiments of the invention hasbeen presented for purposes of illustration and description, and is notintended to be exhaustive or to limit the invention to the precise formdisclosed. The description was selected to best explain the principlesof the invention and their practical application to enable othersskilled in the art to best utilize the invention in various embodimentsand various modifications as are suited to the particular usecontemplated. It is intended that the scope of the invention not belimited by the specification, but be defined claims.

The invention claimed is:
 1. A compound represented by the followingformula (4) or a salt thereof:

wherein, in formula (4), n=2, 3, 4 or 5, m=1 or 2, provided that a casewhere n=2 and m=1 is excluded, X represents O or S, and Y represents thefollowing formula (5) or (6):

wherein, in the above formula (5), Z represents a hydrogen atom, analkyl group having 1 to 4 carbon atoms or a group OR, where R representsa hydrogen atom or an alkyl group having 1 to 4 carbon atoms, providedthat a case where n=3 or 4 and m=1, X is O and Z is H or a methyl groupis excluded, wherein, in the above formula (6), R₁ to R₅ each representa hydrogen atom or a methyl group, and at least two of R₁ to R₅ aremethyl groups.
 2. The compound according to claim 1, wherein Yrepresents formula (5) and Z represents a hydrogen atom or a group OR,where R represents a hydrogen atom or an alkyl group having 1 to 4carbon atoms.
 3. The compound according to claim 1, wherein Y representsformula (5) and Z represents a hydrogen atom.